Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation
A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C–C bond activation and intermolecular allylic substitution was well-organized. The key for this transformati...
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| Published in | Organic letters Vol. 26; no. 20; pp. 4262 - 4267 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
24.05.2024
Amer Chemical Soc |
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| Abstract | A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C–C bond activation and intermolecular allylic substitution was well-organized. The key for this transformation is the in situ generated hydrolysis product of cyclopropenone, which triggered a new reaction with vinylethylene carbonates. The reaction mechanism was investigated, demonstrating the high stereoselectivity and excellent atomic economy in this process. |
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| AbstractList | A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C-C bond activation and intermolecular allylic substitution was well-organized. The key for this transformation is the in situ generated hydrolysis product of cyclopropenone, which triggered a new reaction with vinylethylene carbonates. The reaction mechanism was investigated, demonstrating the high stereoselectivity and excellent atomic economy in this process. A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C-C bond activation and intermolecular allylic substitution was well-organized. The key for this transformation is the generated hydrolysis product of cyclopropenone, which triggered a new reaction with vinylethylene carbonates. The reaction mechanism was investigated, demonstrating the high stereoselectivity and excellent atomic economy in this process. |
| Author | Sun, Wei Sun, Meng Zhang, Zhou Zhang, Shu-Lin Liang, Fei-Fei Zhou, An-Xi |
| AuthorAffiliation | Key Laboratory of Synthetic and Natural Functional Molecule of Ministry of Education, College of Chemistry and Materials Science Northwest University Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province |
| AuthorAffiliation_xml | – name: Northwest University – name: Key Laboratory of Synthetic and Natural Functional Molecule of Ministry of Education, College of Chemistry and Materials Science – name: Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province |
| Author_xml | – sequence: 1 givenname: Zhou surname: Zhang fullname: Zhang, Zhou organization: Northwest University – sequence: 2 givenname: Fei-Fei surname: Liang fullname: Liang, Fei-Fei organization: Northwest University – sequence: 3 givenname: Shu-Lin surname: Zhang fullname: Zhang, Shu-Lin organization: Northwest University – sequence: 4 givenname: Wei surname: Sun fullname: Sun, Wei organization: Northwest University – sequence: 5 givenname: An-Xi surname: Zhou fullname: Zhou, An-Xi email: zhouanxi@hotmail.com organization: Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province – sequence: 6 givenname: Meng orcidid: 0000-0003-0257-4174 surname: Sun fullname: Sun, Meng email: sunmeng@nwu.edu.cn organization: Northwest University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38722897$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/acs.orglett.9b04656 10.1021/jacs.7b04759 10.1021/acs.chemrev.6b00599 10.1038/s41467-020-16084-0 10.1021/acs.orglett.7b03247 10.1002/anie.201711648 10.1021/jacs.9b13026 10.1021/cr010011q 10.1021/acs.orglett.1c02597 10.1021/acs.joc.0c02700 10.1021/acs.accounts.7b00150 10.1021/cr0100244 10.1021/acs.orglett.0c02099 10.1021/jacs.0c00078 10.1002/anie.201804160 10.1039/d1sc01115d 10.1016/j.trechm.2019.12.002 10.1039/c9cc08926h 10.1021/jacs.1c03182 10.1021/acs.chemrev.6b00554 10.1002/chem.202101839 10.1002/anie.201609658 10.1021/acs.chemrev.0c00151 10.1039/c8cc08081j 10.1002/anie.201910378 10.1021/acscatal.3c03282 10.1016/j.phytochem.2015.05.012 10.1021/ja065868p 10.1021/jacs.7b12608 10.1021/acscatal.2c02872 10.1021/jacs.8b12095 10.1021/acs.accounts.3c00760 10.1021/jacs.6b08841 10.1021/jacs.7b09161 10.1039/d2cc00421f 10.1007/s11426-022-1547-0 10.1021/acs.orglett.8b02612 10.6023/cjoc202207034 10.1002/anie.201603638 10.1016/j.bmcl.2012.07.010 10.1002/cjoc.202300313 10.1021/acs.orglett.0c01211 10.1021/cr400628s 10.1021/acs.orglett.3c01292 10.1039/d3qo00070b 10.1021/acs.orglett.1c03566 10.1038/s41557-021-00746-7 10.1021/acscatal.3c01686 10.1021/acs.joc.9b02253 10.1002/anie.201915021 10.1021/acs.chemrev.5b00138 10.1021/jacs.0c11504 10.1002/anie.201913130 10.1021/np900827a 10.1021/acs.orglett.6b02981 10.1021/jacs.8b00868 10.1002/ajoc.202000193 10.1039/C9CC08926H 10.1039/D2CC00421F 10.1039/D3QO00070B 10.1039/C8CC08081J 10.1021/jacs.6b07382 10.1021/acscatal.2c02667 10.1076/phbi.39.5.332.5895 10.1039/D1SC01115D |
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| Keywords | FUNCTIONALIZATION ENANTIOSELECTIVE SYNTHESIS 3+2 CYCLOADDITION ACCESS SESQUITERPENE LACTONES WATER |
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| References | Zhang, L (WOS:001084813300008) 2023; 41 Yang, LC (WOS:000435766800050) 2018; 57 Ren, JT (WOS:000449443100006) 2018; 20 Zheng, Y (WOS:000612557200055) 2021; 143 Du, QF (WOS:000903967500014) 2022; 42 Fumagalli, G (WOS:000405642800022) 2017; 117 Zeng, Q (WOS:001012186900001) 2023; 13 Nanda, T (WOS:000516667200029) 2020; 22 Khan, A (WOS:000496546800001) 2020; 59 Khan, A (WOS:000407540200027) 2017; 139 Song, BC (WOS:000538526500014) 2020; 142 Bai, DC (WOS:000506215900001) 2020; 59 Zhang, YB (WOS:001004483700001) 2023; 25 Chen, L (WOS:000531425700032) 2020; 11 Wei, Y (WOS:000455561800026) 2019; 141 Nanda, T (WOS:000618540600067) 2021; 86 Rong, ZQ (WOS:000414506400007) 2017; 139 Li, RR (WOS:000674528300002) 2021; 13 Xie, F (WOS:000389224000030) 2016; 55 Shi, YS (WOS:000682394600001) 2021; 27 To, CT (WOS:000406085500022) 2017; 50 Komatsu, K (WOS:000182150900014) 2003; 103 Cai, AJ (WOS:000387095000008) 2016; 138 Lang, G (WOS:000172801000003) 2001; 39 Vicente, R (WOS:000611061700006) 2021; 121 Lin, ZY (WOS:000640671100001) 2021; 12 Liu, BX (WOS:000697348600038) 2021; 23 Wang, X (WOS:001036791800001) 2023; 66 Youn, UJ (WOS:000308046400040) 2012; 22 Nanda, T (WOS:000863208500001) 2022 Raiguru, BP (WOS:000551201200001) 2020; 9 Deng, L (WOS:000521131400003) 2020; 2 Wang, YN (WOS:000423494500029) 2018; 57 Chen, F (WOS:000341544800009) 2014; 114 Tong, Q (WOS:001067266700001) 2023; 13 Ghorai, D (WOS:001198113800001) 2024; 57 Liu, WQ (WOS:000939909800001) 2023; 10 Guo, WS (WOS:000657212800007) 2021; 143 Miao, WH (WOS:000744124300017) 2021; 23 Yuan, TT (WOS:000453911200024) 2019; 55 Guo, WS (WOS:000428356000027) 2018; 140 Guo, WS (WOS:000383642300010) 2016; 55 Hu, H (WOS:000772564700001) 2022; 58 Xu, JL (WOS:000569377600010) 2020; 22 Wender, PA (WOS:000242021700040) 2006; 128 Ke, ML (WOS:000538848600018) 2020; 22 Zhou, P (WOS:000508468900007) 2020; 85 Gómez, JE (WOS:000389396100019) 2016; 18 Shi, YS (WOS:000511328200024) 2020; 56 Wang, YN (WOS:000514255300057) 2020; 142 Kurimoto, S (WOS:000357438200033) 2015; 116 Xie, JN (WOS:000417229000032) 2017; 19 Singha, S (WOS:000427910700016) 2018; 140 Souillart, L (WOS:000361254500012) 2015; 115 Kim, DS (WOS:000405642800013) 2017; 117 Uno, H (WOS:000536953100037) 2020; 59 Alkhatib, R (WOS:000276950000055) 2010; 73 Nakamura, M (WOS:000182150900012) 2003; 103 ref9/cit9 ref1/cit1h ref1/cit1e ref1/cit1d ref1/cit1g ref1/cit1f ref2/cit2c ref8/cit8 ref2/cit2b ref2/cit2a ref1/cit1a ref1/cit1c ref1/cit1b ref5/cit5b ref5/cit5c ref10/cit10 ref5/cit5a ref3/cit3b ref3/cit3c ref3/cit3a ref3/cit3f ref3/cit3g ref3/cit3d ref3/cit3e ref3/cit3j ref3/cit3k ref3/cit3h ref3/cit3i ref5/cit5j ref3/cit3l ref5/cit5h ref3/cit3m ref5/cit5i ref5/cit5f ref5/cit5g ref5/cit5d ref5/cit5e ref6/cit6h ref6/cit6i ref6/cit6j ref6/cit6k ref6/cit6d ref4/cit4a ref6/cit6e ref4/cit4b ref6/cit6f ref4/cit4c ref6/cit6g ref6/cit6p ref6/cit6l ref6/cit6m ref6/cit6n ref6/cit6o ref4/cit4d ref6/cit6a ref6/cit6b ref6/cit6c ref7/cit7 |
| References_xml | – volume: 22 start-page: 1368 year: 2020 ident: WOS:000516667200029 article-title: A Palladium-Catalyzed Cascade C-C Activation of Cyclopropenone and Carbonylative Amination: Easy Access to Highly Functionalized Maleimide Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b04656 contributor: fullname: Nanda, T – volume: 139 start-page: 10733 year: 2017 ident: WOS:000407540200027 article-title: Enantioselective Construction of Tertiary C-O Bond via Allylic Substitution of Vinylethylene Carbonates with Water and Alcohols publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b04759 contributor: fullname: Khan, A – volume: 117 start-page: 9404 year: 2017 ident: WOS:000405642800022 article-title: Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.6b00599 contributor: fullname: Fumagalli, G – volume: 11 year: 2020 ident: WOS:000531425700032 article-title: A modular biomimetic strategy for the synthesis of macrolide P-glycoprotein inhibitors via Rh-catalyzed C-H activation publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-020-16084-0 contributor: fullname: Chen, L – volume: 19 start-page: 6388 year: 2017 ident: WOS:000417229000032 article-title: Pd-Catalyzed Enantio- and Regioselective Formation of Allylic Aryl Ethers publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b03247 contributor: fullname: Xie, JN – volume: 57 start-page: 1596 year: 2018 ident: WOS:000423494500029 article-title: Pd-Catalyzed Enantioselective [6+4] Cycloaddition of Vinyl Oxetanes with Azadienes to Access Ten-Membered Heterocycles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201711648 contributor: fullname: Wang, YN – volume: 142 start-page: 3184 year: 2020 ident: WOS:000514255300057 article-title: π-Coordinating Chiral Primary Amine/Palladium Synergistic Catalysis for Asymmetric Allylic Alkylation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.9b13026 contributor: fullname: Wang, YN – volume: 103 start-page: 1371 year: 2003 ident: WOS:000182150900014 article-title: Cyclopropenylium cations, cyclopropenones, and heteroanalogues - Recent advances publication-title: CHEMICAL REVIEWS doi: 10.1021/cr010011q contributor: fullname: Komatsu, K – volume: 23 start-page: 7199 year: 2021 ident: WOS:000697348600038 article-title: Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.1c02597 contributor: fullname: Liu, BX – volume: 86 start-page: 2682 year: 2021 ident: WOS:000618540600067 article-title: Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.0c02700 contributor: fullname: Nanda, T – volume: 50 start-page: 1702 year: 2017 ident: WOS:000406085500022 article-title: Selective Aliphatic Carbon-Carbon Bond Activation by Rhodium Porphyrin Complexes publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.7b00150 contributor: fullname: To, CT – volume: 103 start-page: 1295 year: 2003 ident: WOS:000182150900012 article-title: Cyclopropenone acetals - Synthesis and reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0100244 contributor: fullname: Nakamura, M – volume: 22 start-page: 6739 year: 2020 ident: WOS:000569377600010 article-title: Ag(I)-Catalyzed Addition of Cyclopropenones and Nitrones to Access Imides publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.0c02099 contributor: fullname: Xu, JL – volume: 142 start-page: 9982 year: 2020 ident: WOS:000538526500014 article-title: Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c00078 contributor: fullname: Song, BC – volume: 57 start-page: 7860 year: 2018 ident: WOS:000435766800050 article-title: Palladium-Titanium Relay Catalysis Enables Switch from Alkoxide-π-Allyl to Dienolate Reactivity for Spiro-Heterocycle Synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201804160 contributor: fullname: Yang, LC – volume: 12 start-page: 6712 year: 2021 ident: WOS:000640671100001 article-title: Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes publication-title: CHEMICAL SCIENCE doi: 10.1039/d1sc01115d contributor: fullname: Lin, ZY – volume: 2 start-page: 183 year: 2020 ident: WOS:000521131400003 article-title: Carbon-Carbon Bond Activation of Ketones publication-title: TRENDS IN CHEMISTRY doi: 10.1016/j.trechm.2019.12.002 contributor: fullname: Deng, L – volume: 39 start-page: 332 year: 2001 ident: WOS:000172801000003 article-title: Further sesquiterpene lactones from Eupatorium semialatum publication-title: PHARMACEUTICAL BIOLOGY contributor: fullname: Lang, G – volume: 56 start-page: 1585 year: 2020 ident: WOS:000511328200024 article-title: Divergent C-H activation synthesis of chalcones, quinolones and indoles publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c9cc08926h contributor: fullname: Shi, YS – volume: 143 start-page: 7629 year: 2021 ident: WOS:000657212800007 article-title: Propargylic Amination Enabled the Access to Enantioenriched Acyclic α-Quaternary α-Amino Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.1c03182 contributor: fullname: Guo, WS – volume: 117 start-page: 8977 year: 2017 ident: WOS:000405642800013 article-title: Metal-Organic Cooperative Catalysis in C-H and C-C Bond Activation publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.6b00554 contributor: fullname: Kim, DS – volume: 27 start-page: 13346 year: 2021 ident: WOS:000682394600001 article-title: Divergent Construction of Diverse Scaffolds through Catalyst-Controlled C-H Activation Cascades of Quinazolinones and Cyclopropenones publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.202101839 contributor: fullname: Shi, YS – volume: 55 start-page: 15351 year: 2016 ident: WOS:000389224000030 article-title: Nitrone Directing Groups in Rhodium(III)-Catalyzed C-H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201609658 contributor: fullname: Xie, F – volume: 121 start-page: 162 year: 2021 ident: WOS:000611061700006 article-title: C-C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.0c00151 contributor: fullname: Vicente, R – volume: 55 start-page: 163 year: 2019 ident: WOS:000453911200024 article-title: Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c8cc08081j contributor: fullname: Yuan, TT – volume: 59 start-page: 1340 year: 2020 ident: WOS:000496546800001 article-title: Regio- and Enantioselective Synthesis of Sulfone-Bearing Quaternary Carbon Stereocenters by Pd-Catalyzed Allylic Substitution publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201910378 contributor: fullname: Khan, A – volume: 13 start-page: 12692 year: 2023 ident: WOS:001067266700001 article-title: Toward the Generation of 2-Amino-3-Formyl Difunctionalized Chromones via Pd-Enabled Rearrangement Strategy publication-title: ACS CATALYSIS doi: 10.1021/acscatal.3c03282 contributor: fullname: Tong, Q – volume: 116 start-page: 298 year: 2015 ident: WOS:000357438200033 article-title: Acylated neo-clerodanes and 19-nor-neo-clerodanes from the aerial parts of Scutellaria coleifolia (Lamiaceae) publication-title: PHYTOCHEMISTRY doi: 10.1016/j.phytochem.2015.05.012 contributor: fullname: Kurimoto, S – volume: 128 start-page: 14814 year: 2006 ident: WOS:000242021700040 article-title: Cyclopentadienone synthesis by rhodium(I)-catalyzed [3+2] cycloaddition reactions of cyclopropenones and alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja065868p contributor: fullname: Wender, PA – volume: 140 start-page: 3981 year: 2018 ident: WOS:000428356000027 article-title: A Domino Process toward Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative C(sp3)-C(sp3) Bond Formation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b12608 contributor: fullname: Guo, WS – year: 2022 ident: WOS:000863208500001 article-title: Breaking the Monotony: Cobalt and Maleimide as an Entrant to the Olefin-Mediated Ortho C-H Functionalization br publication-title: ACS CATALYSIS doi: 10.1021/acscatal.2c02872 contributor: fullname: Nanda, T – volume: 141 start-page: 133 year: 2019 ident: WOS:000455561800026 article-title: Enantioselective Trapping of Pd-Containing 1,5-Dipoles by Photogenerated Ketenes: Access to 7-Membered Lactones Bearing Chiral Quaternary Stereocenters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b12095 contributor: fullname: Wei, Y – volume: 57 start-page: 726 year: 2024 ident: WOS:001198113800001 article-title: Vinyl and Alkynyl Substituted Heterocycles as Privileged Scaffolds in Transition Metal Promoted Stereoselective Synthesis publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.3c00760 contributor: fullname: Ghorai, D – volume: 138 start-page: 14194 year: 2016 ident: WOS:000387095000008 article-title: Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b08841 contributor: fullname: Cai, AJ – volume: 139 start-page: 15304 year: 2017 ident: WOS:000414506400007 article-title: Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b09161 contributor: fullname: Rong, ZQ – volume: 58 start-page: 4743 year: 2022 ident: WOS:000772564700001 article-title: Rh(iii)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C-H/C-C bond activation publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/d2cc00421f contributor: fullname: Hu, H – volume: 66 start-page: 2238 year: 2023 ident: WOS:001036791800001 article-title: Synergistic catalysis for stereocontrol of prochiral nucleophiles in palladium-catalyzed asymmetric allylic substitution publication-title: SCIENCE CHINA-CHEMISTRY doi: 10.1007/s11426-022-1547-0 contributor: fullname: Wang, X – volume: 20 start-page: 6636 year: 2018 ident: WOS:000449443100006 article-title: Ag(I)-Catalyzed [3+2]-Annulation of Cyclopropenones and Formamides via C-C Bond Cleavage publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.8b02612 contributor: fullname: Ren, JT – volume: 42 start-page: 3240 year: 2022 ident: WOS:000903967500014 article-title: Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines publication-title: CHINESE JOURNAL OF ORGANIC CHEMISTRY doi: 10.6023/cjoc202207034 contributor: fullname: Du, QF – volume: 55 start-page: 11037 year: 2016 ident: WOS:000383642300010 article-title: Highly Efficient Catalytic Formation of (Z)-1,4-But-2-ene Diols Using Water as a Nucleophile publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201603638 contributor: fullname: Guo, WS – volume: 22 start-page: 5559 year: 2012 ident: WOS:000308046400040 article-title: Anti-inflammatory sesquiterpene lactones from the flower of Vernonia cinerea publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2012.07.010 contributor: fullname: Youn, UJ – volume: 41 start-page: 3003 year: 2023 ident: WOS:001084813300008 article-title: Synthesis of Skipped Aminodienes by a Ni-Catalyzed Ring-Opening/Cross-Coupling Reaction of Vinylaziridines with Multifunctional Organoboronic Acids publication-title: CHINESE JOURNAL OF CHEMISTRY doi: 10.1002/cjoc.202300313 contributor: fullname: Zhang, L – volume: 22 start-page: 4135 year: 2020 ident: WOS:000538848600018 article-title: Palladium-Catalyzed Regio- and Stereoselective Cross-Coupling of Vinylethylene Carbonates with Ketimine Esters to Generate (Z)-Tri- and Tetra-substituted Allylic Amino Acid Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.0c01211 contributor: fullname: Ke, ML – volume: 114 start-page: 8613 year: 2014 ident: WOS:000341544800009 article-title: Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds publication-title: CHEMICAL REVIEWS doi: 10.1021/cr400628s contributor: fullname: Chen, F – volume: 25 start-page: 3922 year: 2023 ident: WOS:001004483700001 article-title: Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.3c01292 contributor: fullname: Zhang, YB – volume: 10 start-page: 1680 year: 2023 ident: WOS:000939909800001 article-title: Pd-catalyzed exclusively regioselective [5+4] cycloaddition for the construction of 1,5-di/ox-azonanes publication-title: ORGANIC CHEMISTRY FRONTIERS doi: 10.1039/d3qo00070b contributor: fullname: Liu, WQ – volume: 23 start-page: 9425 year: 2021 ident: WOS:000744124300017 article-title: Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.1c03566 contributor: fullname: Miao, WH – volume: 13 start-page: 1006 year: 2021 ident: WOS:000674528300002 article-title: A ring expansion strategy towards diverse azaheterocycles publication-title: NATURE CHEMISTRY doi: 10.1038/s41557-021-00746-7 contributor: fullname: Li, RR – volume: 13 start-page: 7514 year: 2023 ident: WOS:001012186900001 article-title: Stereoselective Three-Component Allylic Alkylation Enabled by Dual Photoredox/Ni Catalysis publication-title: ACS CATALYSIS doi: 10.1021/acscatal.3c01686 contributor: fullname: Zeng, Q – volume: 85 start-page: 360 year: 2020 ident: WOS:000508468900007 article-title: Rh(III)-Catalyzed [3+3] Annulation Reaction of Cyclopropenones and Sulfoxonium Ylides toward Trisubstituted 2-Pyrones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.9b02253 contributor: fullname: Zhou, P – volume: 59 start-page: 8187 year: 2020 ident: WOS:000536953100037 article-title: Synthesis of Both Enantiomers of Nine-Membered CF3-Substituted Heterocycles Using a Single Chiral Ligand: Palladium-Catalyzed Decarboxylative Ring Expansion with Kinetic Resolution publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201915021 contributor: fullname: Uno, H – volume: 115 start-page: 9410 year: 2015 ident: WOS:000361254500012 article-title: Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.5b00138 contributor: fullname: Souillart, L – volume: 143 start-page: 1038 year: 2021 ident: WOS:000612557200055 article-title: Enantioselective Inverse Electron Demand (3+2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c11504 contributor: fullname: Zheng, Y – volume: 59 start-page: 2740 year: 2020 ident: WOS:000506215900001 article-title: Nickel(0)-Catalyzed Enantioselective [3+2] Annulation of Cyclopropenones and α,β-Unsaturated Ketones/Imines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201913130 contributor: fullname: Bai, DC – volume: 73 start-page: 780 year: 2010 ident: WOS:000276950000055 article-title: Humulane and Germacrane Sesquiterpenes from Ferula lycia publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np900827a contributor: fullname: Alkhatib, R – volume: 18 start-page: 6042 year: 2016 ident: WOS:000389396100019 article-title: Palladium-Catalyzed Stereoselective Formation of Substituted Allylic Thioethers and Sulfones publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b02981 contributor: fullname: Gómez, JE – volume: 140 start-page: 3551 year: 2018 ident: WOS:000427910700016 article-title: Highly Enantioselective [5+2] Annulations through Cooperative N-Heterocyclic Carbene (NHC) Organocatalysis and Palladium Catalysis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b00868 contributor: fullname: Singha, S – volume: 9 start-page: 1088 year: 2020 ident: WOS:000551201200001 article-title: Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments publication-title: ASIAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ajoc.202000193 contributor: fullname: Raiguru, BP – ident: ref5/cit5f doi: 10.1021/jacs.0c11504 – ident: ref3/cit3i doi: 10.1039/C9CC08926H – ident: ref4/cit4c doi: 10.1021/acs.orglett.0c02099 – ident: ref6/cit6c doi: 10.1002/anie.201603638 – ident: ref1/cit1f doi: 10.1016/j.trechm.2019.12.002 – ident: ref3/cit3l doi: 10.1021/acscatal.3c03282 – ident: ref5/cit5c doi: 10.1021/jacs.7b04759 – ident: ref4/cit4b doi: 10.1021/acs.orglett.8b02612 – ident: ref5/cit5g doi: 10.1002/anie.201910378 – ident: ref3/cit3b doi: 10.1002/anie.201609658 – ident: ref3/cit3k doi: 10.1021/acs.orglett.1c03566 – ident: ref1/cit1a doi: 10.1021/cr400628s – ident: ref1/cit1g doi: 10.1021/acs.chemrev.0c00151 – ident: ref7/cit7 doi: 10.1016/j.phytochem.2015.05.012 – ident: ref6/cit6e doi: 10.1021/acscatal.3c01686 – ident: ref5/cit5a doi: 10.1021/jacs.8b12095 – ident: ref10/cit10 doi: 10.1021/np900827a – ident: ref4/cit4a doi: 10.1039/D2CC00421F – ident: ref5/cit5b doi: 10.1021/jacs.8b00868 – ident: ref1/cit1c doi: 10.1021/acs.accounts.7b00150 – ident: ref3/cit3c doi: 10.1002/anie.201913130 – ident: ref6/cit6m doi: 10.1039/D3QO00070B – ident: ref3/cit3h doi: 10.1039/C8CC08081J – ident: ref1/cit1e doi: 10.1021/acs.chemrev.6b00599 – ident: ref6/cit6g doi: 10.1021/jacs.9b13026 – ident: ref8/cit8 doi: 10.1016/j.bmcl.2012.07.010 – ident: ref3/cit3f doi: 10.1021/acs.joc.9b02253 – ident: ref6/cit6i doi: 10.1021/jacs.7b12608 – ident: ref5/cit5i doi: 10.1002/anie.201711648 – ident: ref6/cit6n doi: 10.1007/s11426-022-1547-0 – ident: ref3/cit3j doi: 10.1002/chem.202101839 – ident: ref6/cit6l doi: 10.1021/acs.accounts.3c00760 – ident: ref6/cit6a doi: 10.1021/jacs.6b07382 – ident: ref6/cit6d doi: 10.1021/acs.orglett.6b02981 – ident: ref3/cit3d doi: 10.1021/acs.orglett.1c02597 – ident: ref1/cit1d doi: 10.1021/acs.chemrev.6b00554 – ident: ref1/cit1b doi: 10.1021/acs.chemrev.5b00138 – ident: ref6/cit6f doi: 10.1038/s41467-020-16084-0 – ident: ref3/cit3m doi: 10.1021/acs.joc.0c02700 – ident: ref5/cit5j doi: 10.1002/anie.201915021 – ident: ref3/cit3a doi: 10.1021/ja065868p – ident: ref1/cit1h doi: 10.1021/acscatal.2c02667 – ident: ref9/cit9 doi: 10.1076/phbi.39.5.332.5895 – ident: ref5/cit5d doi: 10.1021/jacs.7b09161 – ident: ref6/cit6k doi: 10.1021/acs.orglett.0c01211 – ident: ref5/cit5h doi: 10.1002/anie.201804160 – ident: ref2/cit2b doi: 10.1021/cr010011q – ident: ref6/cit6b doi: 10.1021/acs.orglett.7b03247 – ident: ref2/cit2a doi: 10.1021/cr0100244 – ident: ref5/cit5e doi: 10.1021/jacs.6b08841 – ident: ref6/cit6h doi: 10.1021/jacs.0c00078 – ident: ref3/cit3e doi: 10.1038/s41557-021-00746-7 – ident: ref4/cit4d doi: 10.1021/acs.orglett.3c01292 – ident: ref3/cit3g doi: 10.1021/acs.orglett.9b04656 – ident: ref6/cit6p doi: 10.6023/cjoc202207034 – ident: ref6/cit6j doi: 10.1039/D1SC01115D – ident: ref6/cit6o doi: 10.1002/cjoc.202300313 – ident: ref2/cit2c doi: 10.1002/ajoc.202000193 |
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| Snippet | A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation |
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