Copper-catalyzed formal [4+1] annulation of N-propargyl ynamides with diketones
An efficient copper-catalyzed formal [4 + 1] annulation of N-propargyl ynamides with diketones is described. This protocol enables practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to excellent yields under mild reaction conditions. Thus, two new fi...
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| Published in | ORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 1; pp. 203 - 208 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
20.12.2022
Royal Society of Chemistry |
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| Online Access | Get full text |
| ISSN | 2052-4129 2052-4110 2052-4110 |
| DOI | 10.1039/d2qo01786e |
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| Abstract | An efficient copper-catalyzed formal [4 + 1] annulation of N-propargyl ynamides with diketones is described. This protocol enables practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to excellent yields under mild reaction conditions. Thus, two new five-membered heterocycles can be constructed in one step through this vinyl cation chemistry. |
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| AbstractList | An efficient copper-catalyzed formal [4 + 1] annulation of N-propargyl ynamides with diketones is described. This protocol enables practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to excellent yields under mild reaction conditions. Thus, two new five-membered heterocycles can be constructed in one step through this vinyl cation chemistry. |
| Author | Zhu, Xin-Qi Zhou, Bo Xu, Hao-Jin Chen, Can-Ming Ye, Long-Wu Li, Cui-Ting Chen, Jie |
| Author_xml | – sequence: 1 givenname: Hao-Jin surname: Xu fullname: Xu, Hao-Jin organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 2 givenname: Cui-Ting surname: Li fullname: Li, Cui-Ting organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 3 givenname: Can-Ming surname: Chen fullname: Chen, Can-Ming organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 4 givenname: Jie surname: Chen fullname: Chen, Jie organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 5 givenname: Xin-Qi surname: Zhu fullname: Zhu, Xin-Qi email: xinqizhu@xmu.edu.cn organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 6 givenname: Bo surname: Zhou fullname: Zhou, Bo organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China – sequence: 7 givenname: Long-Wu orcidid: 0000-0003-3108-2611 surname: Ye fullname: Ye, Long-Wu email: longwuye@xmu.edu.cn organization: Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China |
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| CitedBy_id | crossref_primary_10_1039_D3CC04817A crossref_primary_10_1039_D4QO02371D crossref_primary_10_1039_D4QO00301B crossref_primary_10_1007_s11426_024_2475_3 crossref_primary_10_1021_acs_joc_3c01990 crossref_primary_10_1039_D3SC04445A crossref_primary_10_1038_s42004_023_00999_y crossref_primary_10_1016_j_jpowsour_2024_235691 crossref_primary_10_1021_acs_orglett_4c00829 crossref_primary_10_1039_D3CC01403G crossref_primary_10_1039_D4QO01623H |
| Cites_doi | 10.1021/jacs.0c01918 10.1021/ar500015k 10.1002/anie.202210637 10.1021/acs.accounts.0c00417 10.1039/c4ob02556c 10.1038/s41557-021-00778-z 10.1021/jacs.9b09303 10.1002/anie.201810701 10.1021/acs.chemrev.5b00121 10.1002/adsc.201600005 10.1021/jacs.9b13975 10.1021/ar400193g 10.1039/c6cs00023a 10.1016/j.tet.2008.04.074 10.1039/d2qo00698g 10.1016/j.xcrp.2021.100448 10.1002/cjoc.202000218 10.1039/c6cc01562j 10.1016/j.tetlet.2017.12.062 10.1002/anie.202007206 10.1055/s-0037-1611647 10.1002/anie.202113464 10.1021/cr5006974 10.1007/s11426-021-1069-7 10.1002/cjoc.201900478 10.1021/ar800104y 10.1002/anie.202204603 10.1002/anie.202201436 10.1039/d0cs00474j 10.1021/acs.orglett.1c03830 10.1002/ejoc.202000023 10.1021/acs.orglett.1c03092 10.1039/d0cs00769b 10.1039/b816701j 10.2174/1385272819666150810225618 10.1021/acs.orglett.8b00888 10.1021/cs400437s 10.1021/acscatal.9b01851 10.1007/s11172-016-1566-x 10.1039/d1sc02773e 10.1021/acscatal.0c04180 10.24820/ark.5550190.p010.416 10.1002/anie.202115554 10.1039/d0cs00283f |
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| References | Li, HH (WOS:000508652100001) 2020; 38 Hong, FL (WOS:000529156100050) 2020; 142 Padwa, A (WOS:000441863800004) 2018 Wang, XN (WOS:000331775200026) 2014; 47 Gagosz, F (WOS:000459926800008) 2019; 51 Asiri, AM (WOS:000381438600004) 2016; 45 Zhu, GY (WOS:000792449400001) 2022; 61 Chen, PF (WOS:000719981600001) 2021; 60 Lynch, CC (WOS:000596472400006) 2020; 49 Chen, YB (WOS:000598713800002) 2020; 49 Huang, EH (WOS:000735955400001) 2022; 24 Zhang, YQ (WOS:000706045700004) 2021; 13 Braun, I (WOS:000322852900027) 2013; 3 Liu, Y (WOS:000363986500005) 2016; 20 Kaur, T (WOS:000377084900001) 2016; 52 Zhu, GY (WOS:000709693500071) 2021; 23 Hashmi, ASK (WOS:000333235800015) 2014; 47 Wang, ZS (WOS:000515214000046) 2020; 142 Zhang, YQ (WOS:000665056400010) 2021; 2 Zhu, BH (WOS:000692430700001) 2021; 64 Padwa, A (WOS:000271033400009) 2009; 38 Zhou, B (WOS:000474812400059) 2019; 9 Ushakov, PY (WOS:000840924300001) 2022; 9 Luo, J (WOS:000598140200022) 2020; 10 Zhu, XQ (WOS:000663879300001) 2021; 12 Zhang, ZH (WOS:000257500500001) 2008; 64 Wang, ZS (WOS:000769511500001) 2022; 61 Hong, FL (WOS:000492800500051) 2019; 141 Liu, X (WOS:000559994700001) 2020; 59 Qi, LJ (WOS:000847820400001) 2022; 61 Huang, EH (WOS:000569922900010) 2020; 38 Zhang, H (WOS:000521413700001) 2020; 2020 Zhu, C (WOS:000424074700002) 2018; 59 Evano, G (WOS:000366962600001) 2015; 48 Day, DP (WOS:000375880200003) 2016; 358 Hong, FL (WOS:000733408800001) 2022; 61 Hu, YC (WOS:000624298500011) 2021; 50 Liao, SH (WOS:000340702000004) 2014; 47 Zhu, CY (WOS:000350144600004) 2015; 13 Niggemann, M (WOS:000454575500003) 2018; 57 Padwa, A (WOS:000400400700008) 2016; 65 Hong, FL (WOS:000572833000027) 2020; 53 Jiang, HF (WOS:000434367500004) 2018; 20 Chen, JR (WOS:000356316300016) 2015; 115 Ford, A (WOS:000361935700007) 2015; 115 |
| References_xml | – volume: 142 start-page: 7618 year: 2020 ident: WOS:000529156100050 article-title: Copper-Catalyzed Asymmetric Reaction of Alkenyl Diynes with Styrenes by Formal [3+2] Cycloaddition via Cu-Containing AllCarbon 1,3-Dipoles: Access to Chiral Pyrrole-Fused Bridged [2.2.1] Skeletons publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c01918 – volume: 47 start-page: 864 year: 2014 ident: WOS:000333235800015 article-title: Dual Gold Catalysis publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar500015k – volume: 61 start-page: ARTN e202210637 year: 2022 ident: WOS:000847820400001 article-title: Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202210637 – volume: 48 start-page: 59 year: 2015 ident: WOS:000366962600001 article-title: Ynamides: Powerful and Versatile Reagents for Chemical Synthesis publication-title: ALDRICHIMICA ACTA – volume: 53 start-page: 2003 year: 2020 ident: WOS:000572833000027 article-title: Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.0c00417 – volume: 13 start-page: 2530 year: 2015 ident: WOS:000350144600004 article-title: Ylide formal [4+1] annulation publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c4ob02556c – volume: 13 start-page: 1093 year: 2021 ident: WOS:000706045700004 article-title: Asymmetric dearomatization catalysed by chiral Bronsted acids via activation of ynamides publication-title: NATURE CHEMISTRY doi: 10.1038/s41557-021-00778-z – volume: 141 start-page: 16961 year: 2019 ident: WOS:000492800500051 article-title: Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.9b09303 – volume: 57 start-page: 16942 year: 2018 ident: WOS:000454575500003 article-title: Are Vinyl Cations Finally Coming of Age? publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201810701 – volume: 115 start-page: 9981 year: 2015 ident: WOS:000361935700007 article-title: Modern Organic Synthesis with α-Diazocarbonyl Compounds publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.5b00121 – volume: 358 start-page: 1368 year: 2016 ident: WOS:000375880200003 article-title: Gold-Catalyzed Cycloisomerizations of 1,n-Diyne Carbonates and Esters publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201600005 – volume: 142 start-page: 3636 year: 2020 ident: WOS:000515214000046 article-title: Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.9b13975 – volume: 47 start-page: 560 year: 2014 ident: WOS:000331775200026 article-title: Ynamides in Ring Forming Transformations publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar400193g – volume: 45 start-page: 4471 year: 2016 ident: WOS:000381438600004 article-title: Gold-catalysed reactions of diynes publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c6cs00023a – volume: 64 start-page: 6577 year: 2008 ident: WOS:000257500500001 article-title: Recent studies on the reactions of α-diazocarbonyl compounds publication-title: TETRAHEDRON doi: 10.1016/j.tet.2008.04.074 – volume: 9 start-page: 5358 year: 2022 ident: WOS:000840924300001 article-title: Recent advances in the application of ylide-like species in [4+1]-annulation reactions: an updated review publication-title: ORGANIC CHEMISTRY FRONTIERS doi: 10.1039/d2qo00698g – volume: 2 start-page: ARTN 100448 year: 2021 ident: WOS:000665056400010 article-title: Rapid and practical access to diverse quindolines by catalyst-free and regioselectivity-reversed Povarov reaction publication-title: CELL REPORTS PHYSICAL SCIENCE doi: 10.1016/j.xcrp.2021.100448 – volume: 38 start-page: 1086 year: 2020 ident: WOS:000569922900010 article-title: Copper-CatalyzedCarbocyclization of Silyl Enol Ether Tethered Ynamides for Efficient and Practical Synthesis of2-Azabicyclo[3.2.0] Compounds† publication-title: CHINESE JOURNAL OF CHEMISTRY doi: 10.1002/cjoc.202000218 – volume: 52 start-page: 6958 year: 2016 ident: WOS:000377084900001 article-title: Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs) publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c6cc01562j – volume: 59 start-page: 430 year: 2018 ident: WOS:000424074700002 article-title: Recent advance in transition-metal-catalyzed oxidant-free 4+1 annulation through C-H bond activation publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2017.12.062 – volume: 59 start-page: 17984 year: 2020 ident: WOS:000559994700001 article-title: Copper-Catalyzed Azide-Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202007206 – volume: 51 start-page: 1087 year: 2019 ident: WOS:000459926800008 article-title: Gold Vinylidenes as Useful Intermediates in Synthetic Organic Chemistry publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0037-1611647 – volume: 60 start-page: 27164 year: 2021 ident: WOS:000719981600001 article-title: Bronsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202113464 – volume: 115 start-page: 5301 year: 2015 ident: WOS:000356316300016 article-title: Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems publication-title: CHEMICAL REVIEWS doi: 10.1021/cr5006974 – volume: 64 start-page: 1985 year: 2021 ident: WOS:000692430700001 article-title: Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams publication-title: SCIENCE CHINA-CHEMISTRY doi: 10.1007/s11426-021-1069-7 – volume: 38 start-page: 263 year: 2020 ident: WOS:000508652100001 article-title: Efficient and Divergent Synthesis of Medium-Sized Lactams through Zinc-Catalyzed Oxidative Cyclization of Indoly Ynamides publication-title: CHINESE JOURNAL OF CHEMISTRY doi: 10.1002/cjoc.201900478 – volume: 47 start-page: 2260 year: 2014 ident: WOS:000340702000004 article-title: Side Arm Strategy for Catalyst Design: Modifying Bisoxazolines for Remote Control of Enantioselection and Related publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar800104y – volume: 61 start-page: ARTN e202204603 year: 2022 ident: WOS:000792449400001 article-title: Catalyst-Dependent Stereospecific [3,3]-Sigmatropic Rearrangement of Sulfoxide-Ynamides: Divergent Synthesis of Chiral Medium-Sized N,S-Heterocycles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202204603 – volume: 61 start-page: ARTN e202201436 year: 2022 ident: WOS:000769511500001 article-title: Synthesis of Axially Chiral N-Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Bronsted Acids publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202201436 – volume: 49 start-page: 8897 year: 2020 ident: WOS:000598713800002 article-title: Bronsted acid-mediated reactions of ynamides publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/d0cs00474j – volume: 24 start-page: 196 year: 2022 ident: WOS:000735955400001 article-title: Copper-Catalyzed Si-H Bond Insertion Reaction of N-Propargyl Ynamides with Hydrosilanes publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.1c03830 – volume: 2020 start-page: 4098 year: 2020 ident: WOS:000521413700001 article-title: Recent Advances in Phosphine-Promoted (4+1) Annulation Reactions publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.202000023 – volume: 23 start-page: 8067 year: 2021 ident: WOS:000709693500071 article-title: Copper-Catalyzed Cyclization of N-Propargyl Ynamides with Borane Adducts through B-H Bond Insertion publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.1c03092 – volume: 49 start-page: 8543 year: 2020 ident: WOS:000596472400006 article-title: Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/d0cs00769b – volume: 38 start-page: 3072 year: 2009 ident: WOS:000271033400009 article-title: Domino reactions of rhodium(II) carbenoids for alkaloid synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b816701j – volume: 20 start-page: 19 year: 2016 ident: WOS:000363986500005 article-title: Recent Advances in Catalytic Selective Synthesis of Epoxide and Aziridine via Diazocarbonyl Compound publication-title: CURRENT ORGANIC CHEMISTRY doi: 10.2174/1385272819666150810225618 – volume: 20 start-page: 3166 year: 2018 ident: WOS:000434367500004 article-title: Two C-O Bond Formations on a Carbenic Carbon: Palladium-Catalyzed Coupling of N-Tosylhydrazones and Benzo-1,2-quinones To Construct Benzodioxoles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.8b00888 – volume: 3 start-page: 1902 year: 2013 ident: WOS:000322852900027 article-title: Gold Catalysis 2.0 publication-title: ACS CATALYSIS doi: 10.1021/cs400437s – volume: 9 start-page: 6393 year: 2019 ident: WOS:000474812400059 article-title: Reversal of Regioselectivity in Ynamide Chemistry publication-title: ACS CATALYSIS doi: 10.1021/acscatal.9b01851 – volume: 65 start-page: 2183 year: 2016 ident: WOS:000400400700008 article-title: Cycloaddition chemistry of carbonyl ylides for alkaloid synthesis publication-title: RUSSIAN CHEMICAL BULLETIN doi: 10.1007/s11172-016-1566-x – volume: 12 start-page: 9466 year: 2021 ident: WOS:000663879300001 article-title: Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights publication-title: CHEMICAL SCIENCE doi: 10.1039/d1sc02773e – volume: 10 start-page: 13978 year: 2020 ident: WOS:000598140200022 article-title: Exploiting Remarkable Reactivities of Ynamides: Opportunities in Designing Catalytic Enantioselective Reactions publication-title: ACS CATALYSIS doi: 10.1021/acscatal.0c04180 – start-page: 23 year: 2018 ident: WOS:000441863800004 article-title: Use of nitrogen and oxygen dipole ylides for alkaloid synthesis publication-title: ARKIVOC doi: 10.24820/ark.5550190.p010.416 – volume: 61 start-page: ARTN e202115554 year: 2022 ident: WOS:000733408800001 article-title: Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202115554 – volume: 50 start-page: 2582 year: 2021 ident: WOS:000624298500011 article-title: Reactivity of ynamides in catalytic intermolecular annulations publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/d0cs00283f |
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| Title | Copper-catalyzed formal [4+1] annulation of N-propargyl ynamides with diketones |
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