Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst
The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source....
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Published in | Organic letters Vol. 22; no. 10; pp. 3765 - 3769 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
15.05.2020
Amer Chemical Soc |
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Abstract | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. |
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AbstractList | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. |
Author | Rueping, Magnus Ganardi, Ruth-Christine Brzozowska, Aleksandra Zubar, Viktoriia |
AuthorAffiliation | King Abdullah University of Science and Technology (KAUST) KAUST Catalysis Center (KCC) Institute of Organic Chemistry |
AuthorAffiliation_xml | – name: KAUST Catalysis Center (KCC) – name: King Abdullah University of Science and Technology (KAUST) – name: Institute of Organic Chemistry |
Author_xml | – sequence: 1 givenname: Aleksandra surname: Brzozowska fullname: Brzozowska, Aleksandra organization: Institute of Organic Chemistry – sequence: 2 givenname: Viktoriia surname: Zubar fullname: Zubar, Viktoriia organization: Institute of Organic Chemistry – sequence: 3 givenname: Ruth-Christine surname: Ganardi fullname: Ganardi, Ruth-Christine organization: Institute of Organic Chemistry – sequence: 4 givenname: Magnus orcidid: 0000-0003-4580-5227 surname: Rueping fullname: Rueping, Magnus email: magnus.rueping@rwth-aachen.de organization: King Abdullah University of Science and Technology (KAUST) |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32227972$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1002/anie.201810885 10.1126/science.1214451 10.1039/c3cc46727a 10.1021/om0110078 10.1021/acscatal.6b00993 10.1002/cssc.201802416 10.1039/c7cs00693d 10.1021/acs.orglett.8b03506 10.1002/anie.201805630 10.1021/op2002613 10.1021/acsomega.7b00713 10.1002/anie.201704184 10.1021/acs.accounts.8b00149 10.1021/jacs.7b00879 10.1002/anie.201709010 10.1021/acscatal.8b02240 10.1021/acs.orglett.8b01179 10.1055/s-2004-829165 10.1021/ja4116346 10.1021/ol400990u 10.1002/anie.201805483 10.1021/acs.chemrev.5b00162 10.1038/s41467-018-06831-9 10.1002/cctc.201800553 10.1055/s-0036-1590818 10.1039/c7gc02006f 10.1002/anie.201704682 10.1002/ejoc.201600018 10.1002/cssc.201801660 10.1039/c7cs00334j 10.1021/jacs.5b00936 10.1021/acs.inorgchem.5b01825 10.1002/cctc.201402693 10.1055/s-0033-1339299 10.1055/s-2005-861874 10.1021/ja4108148 10.1021/ja046753t 10.1016/j.ccr.2015.06.015 10.1002/ejoc.201700376 10.1021/acs.joc.9b00792 10.1002/anie.201607579 10.1002/cctc.201701722 10.1039/c3cs60197h 10.1021/acscatal.8b00983 10.1021/cr00039a007 10.1039/C7CS00334J 10.1021/ja00851a038 10.1039/C7CS00693D 10.1016/S0040-4039(00)82050-X 10.1021/jo00376a042 10.1002/9781118839621 10.1039/C7GC02006F 10.1021/acscatal.8b02869 10.1039/C3CS60197H 10.1021/jo00038a044 |
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References | Cherney, AH (WOS:000361254500015) 2015; 115 Zubar, V (WOS:000446306600008) 2018; 57 Peris, E (WOS:000429201500003) 2018; 47 Van Koten, G. (000535292300006.45) 2014 Brzozowska, A (WOS:000431727300043) 2018; 8 Mukhopadhyay, TK (WOS:000398764000045) 2017; 139 Wang, CM (WOS:000432900200071) 2018; 20 Borghs, JC (WOS:000455285800016) 2019; 21 Liu, WP (WOS:000377326700043) 2016; 6 Greenhalgh, MD (WOS:000347781400001) 2015; 7 Stradiotto, M. (000535292300006.40) 2016 Garbe, M (WOS:000407822200002) 2017; 2017 TUCKER, CE (WOS:A1992HX97100044) 1992; 57 Marion, P (WOS:000414147100001) 2017; 19 Obligacion, JV (WOS:000329137300016) 2013; 135 Shirakawa, K (WOS:000223208100018) 2004 Lennox, AJJ (WOS:000329070600022) 2014; 43 Maji, B (WOS:000406065500024) 2017; 49 (WOS:000463067300035) 2018 Reardon, D (WOS:000174203400004) 2002; 21 Obligacion, JV (WOS:000354910500001) 2015; 137 Gorgas, N (WOS:000436027200025) 2018; 51 Carney, JR (WOS:000440899000035) 2018; 57 Greenhalgh, MD (WOS:000326741200030) 2013; 49 Tondreau, AM (WOS:000299769200039) 2012; 335 Wang, CY (WOS:000330531300002) 2013; 24 Mukherjee, S (WOS:000444364800123) 2018; 8 Carney, JR (WOS:000382962700001) 2016; 2016 Zell, T (WOS:000431974000002) 2018; 10 BROWN, HC (WOS:A1986F587600042) 1986; 51 Sklyaruk, J (WOS:000455033700019) 2019; 58 Kallmeier, F (WOS:000418798600005) 2018; 57 Ghosh, C (WOS:000364175000033) 2015; 54 Ma, XC (WOS:000409924000068) 2017; 2 Mukhopadhyay, TK (WOS:000330202300016) 2014; 136 Trost, BM (WOS:000228616300001) 2005 Valyaev, DA (WOS:000367412000007) 2016; 308 Vasilenko, V (WOS:000404739200012) 2017; 56 Erken, C (WOS:000448710400015) 2018; 9 Bart, SC (WOS:000224685200058) 2004; 126 Fan, RQ (WOS:000292178000003) 2011; 32 Borghs, JC (WOS:000473116200033) 2019; 84 Wang, CM (WOS:000406798700054) 2017; 56 SATOH, Y (WOS:A1988N097400019) 1988; 29 El-Sepelgy, O (WOS:000477706600034) 2019; 12 Borghs, JC (WOS:000477706600031) 2019; 12 Zhang, GQ (WOS:000387028000030) 2016; 55 MIYAURA, N (WOS:A1995TD89200007) 1995; 95 Obligacion, JV (WOS:000320298900029) 2013; 15 Skoda, EM (WOS:000299238700003) 2012; 16 Filonenko, GA (WOS:000425374900010) 2018; 47 Wang, CM (WOS:000436933700020) 2018; 10 BROWN, HC (WOS:A1975AP07200038) 1975; 97 ref3/cit3 ref13/cit13a ref16/cit16 ref13/cit13b ref13/cit13c ref13/cit13d ref13/cit13e ref12/cit12c ref12/cit12b ref12/cit12a ref2/cit2b ref2/cit2a ref17/cit17 ref11/cit11c ref11/cit11b ref11/cit11e ref11/cit11d Fan R.-Q. (ref15/cit15) 2011; 32 ref11/cit11a Van Koten G. (ref10/cit10c) 2014 ref6/cit6 ref9/cit9c ref10/cit10d ref9/cit9b ref9/cit9a ref8/cit8a ref8/cit8c ref8/cit8b ref8/cit8e ref8/cit8d ref9/cit9j ref8/cit8g ref9/cit9i Stradiotto M. (ref10/cit10b) 2016 ref8/cit8f ref9/cit9h ref8/cit8i ref9/cit9g ref5/cit5 ref8/cit8h ref9/cit9f ref8/cit8k ref9/cit9e ref8/cit8j ref9/cit9d ref4/cit4a ref4/cit4b ref4/cit4c ref14/cit14a ref14/cit14b ref1/cit1 Morales-Morales D. (ref10/cit10a) 2018 ref7/cit7 |
References_xml | – volume: 58 start-page: 775 year: 2019 ident: WOS:000455033700019 article-title: Catalytic C-1 Alkylation with Methanol and Isotope-Labeled Methanol publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201810885 contributor: fullname: Sklyaruk, J – volume: 97 start-page: 5249 year: 1975 ident: WOS:A1975AP07200038 article-title: HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BROWN, HC – start-page: 1 year: 2018 ident: WOS:000463067300035 article-title: Pincer Compounds: Chemistry and Applications publication-title: PINCER COMPOUNDS: CHEMISTRY AND APPLICATIONS – volume: 335 start-page: 567 year: 2012 ident: WOS:000299769200039 article-title: Iron Catalysts for Selective Anti-Markovnikov Alkene Hydrosilylation Using Tertiary Silanes publication-title: SCIENCE doi: 10.1126/science.1214451 contributor: fullname: Tondreau, AM – volume: 49 start-page: 11230 year: 2013 ident: WOS:000326741200030 article-title: Chemo-, regio-, and stereoselective iron- catalysed hydroboration of alkenes and alkynes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c3cc46727a contributor: fullname: Greenhalgh, MD – volume: 21 start-page: 786 year: 2002 ident: WOS:000174203400004 article-title: Mono- and zerovalent manganese alkyl complexes supported by the alpha,alpha '-diiminato pyridine ligand: Alkyl stabilization at the expense of catalytic performance publication-title: ORGANOMETALLICS doi: 10.1021/om0110078 contributor: fullname: Reardon, D – volume: 95 start-page: 2457 year: 1995 ident: WOS:A1995TD89200007 article-title: PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS publication-title: CHEMICAL REVIEWS contributor: fullname: MIYAURA, N – volume: 6 start-page: 3743 year: 2016 ident: WOS:000377326700043 article-title: Manganese-Catalyzed C-H Activation publication-title: ACS CATALYSIS doi: 10.1021/acscatal.6b00993 contributor: fullname: Liu, WP – volume: 12 start-page: 3083 year: 2019 ident: WOS:000477706600031 article-title: Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation publication-title: CHEMSUSCHEM doi: 10.1002/cssc.201802416 contributor: fullname: Borghs, JC – volume: 47 start-page: 1959 year: 2018 ident: WOS:000429201500003 article-title: Key factors in pincer ligand design publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c7cs00693d contributor: fullname: Peris, E – volume: 21 start-page: 70 year: 2019 ident: WOS:000455285800016 article-title: Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.8b03506 contributor: fullname: Borghs, JC – volume: 57 start-page: 13439 year: 2018 ident: WOS:000446306600008 article-title: Hydrogenation of CO2-Derived Carbonates and Polycarbonates to Methanol and Diols by Metal-Ligand Cooperative Manganese Catalysis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201805630 contributor: fullname: Zubar, V – volume: 32 start-page: 1239 year: 2011 ident: WOS:000292178000003 article-title: Syntheses, Crystal Structures and Catalytic Performance of 2,6-Bis(imino) pyridyl Manganese Complexes publication-title: CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE contributor: fullname: Fan, RQ – volume: 16 start-page: 26 year: 2012 ident: WOS:000299238700003 article-title: Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres publication-title: ORGANIC PROCESS RESEARCH & DEVELOPMENT doi: 10.1021/op2002613 contributor: fullname: Skoda, EM – volume: 51 start-page: 5277 year: 1986 ident: WOS:A1986F587600042 article-title: VINYLIC ORGANOBORANES .7. STEREOSELECTIVE SYNTHESIS OF (E)-(1-SUBSTITUTED-1-ALKENYL)BORONIC ESTERS BY THE NUCLEOPHILIC-SUBSTITUTION OF (Z)-(1-BROMO-1-ALKENYL)BORONIC ESTERS WITH ORGANOLITHIUM OR GRIGNARD-REAGENTS - ISOLATION AND OXIDATION TO KETONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BROWN, HC – volume: 2 start-page: 4688 year: 2017 ident: WOS:000409924000068 article-title: Manganese-Catalyzed Asymmetric Hydrosilylation of Aryl Ketones publication-title: ACS OMEGA doi: 10.1021/acsomega.7b00713 contributor: fullname: Ma, XC – volume: 56 start-page: 8393 year: 2017 ident: WOS:000404739200012 article-title: Mechanism-Based Enantiodivergence in Manganese Reduction Catalysis: A Chiral Pincer Complex for the Highly Enantioselective Hydroboration of Ketones publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201704184 contributor: fullname: Vasilenko, V – volume: 51 start-page: 1558 year: 2018 ident: WOS:000436027200025 article-title: Isoelectronic Manganese and Iron Hydrogenation/Dehydrogenation Catalysts: Similarities and Divergences publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.8b00149 contributor: fullname: Gorgas, N – volume: 139 start-page: 4901 year: 2017 ident: WOS:000398764000045 article-title: Mechanistic Investigation of Bis(imino)pyridine Manganese Catalyzed Carbonyl and Carboxylate Hydrosilylation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b00879 contributor: fullname: Mukhopadhyay, TK – volume: 57 start-page: 46 year: 2018 ident: WOS:000418798600005 article-title: Manganese Complexes for (De)Hydrogenation Catalysis: A Comparison to Cobalt and Iron Catalysts publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201709010 contributor: fullname: Kallmeier, F – volume: 8 start-page: 8915 year: 2018 ident: WOS:000444364800123 article-title: O-2 Reduction by Biosynthetic Models of Cytochrome c Oxidase: Insights into Role of Proton Transfer Residues from Perturbed Active Sites Models of CcO publication-title: ACS CATALYSIS doi: 10.1021/acscatal.8b02240 contributor: fullname: Mukherjee, S – volume: 20 start-page: 3105 year: 2018 ident: WOS:000432900200071 article-title: Manganese Catalyzed Regioselective C-H Alkylation: Experiment and Computation publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.8b01179 contributor: fullname: Wang, CM – start-page: 1814 year: 2004 ident: WOS:000223208100018 article-title: Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-2004-829165 contributor: fullname: Shirakawa, K – volume: 136 start-page: 882 year: 2014 ident: WOS:000330202300016 article-title: A Highly Active Manganese Precatalyst for the Hydrosilylation of Ketones and Esters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja4116346 contributor: fullname: Mukhopadhyay, TK – volume: 15 start-page: 2680 year: 2013 ident: WOS:000320298900029 article-title: Highly Selective Bis(imino)pyridine Iron-Catalyzed Alkene Hydroboration publication-title: ORGANIC LETTERS doi: 10.1021/ol400990u contributor: fullname: Obligacion, JV – volume: 57 start-page: 10620 year: 2018 ident: WOS:000440899000035 article-title: Manganese-Catalyzed Hydrofunctionalization of Alkenes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201805483 contributor: fullname: Carney, JR – volume: 115 start-page: 9587 year: 2015 ident: WOS:000361254500015 article-title: Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.5b00162 contributor: fullname: Cherney, AH – volume: 9 start-page: ARTN 4521 year: 2018 ident: WOS:000448710400015 article-title: Manganese-catalyzed hydroboration of carbon dioxide and other challenging carbonyl groups publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-018-06831-9 contributor: fullname: Erken, C – volume: 10 start-page: 2681 year: 2018 ident: WOS:000436933700020 article-title: Rhenium- and Manganese-Catalyzed Selective Alkenylation of Indoles publication-title: CHEMCATCHEM doi: 10.1002/cctc.201800553 contributor: fullname: Wang, CM – volume: 49 start-page: 3377 year: 2017 ident: WOS:000406065500024 article-title: Recent Developments of Manganese Complexes for Catalytic Hydrogenation and Dehydrogenation Reactions publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0036-1590818 contributor: fullname: Maji, B – volume: 19 start-page: 4973 year: 2017 ident: WOS:000414147100001 article-title: Sustainable chemistry: how to produce better and more from less? publication-title: GREEN CHEMISTRY doi: 10.1039/c7gc02006f contributor: fullname: Marion, P – year: 2014 ident: 000535292300006.45 publication-title: Organometallic Pincer Chemistry contributor: fullname: Van Koten, G. – volume: 56 start-page: 9935 year: 2017 ident: WOS:000406798700054 article-title: Manganese-Catalyzed C-H Functionalizations: eHydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201704682 contributor: fullname: Wang, CM – volume: 57 start-page: 3482 year: 1992 ident: WOS:A1992HX97100044 article-title: MILD AND STEREOSELECTIVE HYDROBORATIONS OF FUNCTIONALIZED ALKYNES AND ALKENES USING PINACOLBORANE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: TUCKER, CE – volume: 2016 start-page: 3912 year: 2016 ident: WOS:000382962700001 article-title: Recent Advances of Manganese Catalysis for Organic Synthesis publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201600018 contributor: fullname: Carney, JR – volume: 12 start-page: 3099 year: 2019 ident: WOS:000477706600034 article-title: C-Alkylation of Secondary Alcohols by Primary Alcohols through Manganese-Catalyzed Double Hydrogen Autotransfer publication-title: CHEMSUSCHEM doi: 10.1002/cssc.201801660 contributor: fullname: El-Sepelgy, O – volume: 47 start-page: 1459 year: 2018 ident: WOS:000425374900010 article-title: Catalytic (de)hydrogenation promoted by non-precious metals - Co, Fe and Mn: recent advances in an emerging field publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c7cs00334j contributor: fullname: Filonenko, GA – volume: 137 start-page: 5855 year: 2015 ident: WOS:000354910500001 article-title: Cobalt Catalyzed Z-Selective Hydroboration of Terminal Alkynes and Elucidation of the Origin of Selectivity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b00936 contributor: fullname: Obligacion, JV – volume: 54 start-page: 10398 year: 2015 ident: WOS:000364175000033 article-title: A Pentacoordinate Mn(II) Precatalyst That Exhibits Notable Aldehyde and Ketone Hydrosilylation Turnover Frequencies publication-title: INORGANIC CHEMISTRY doi: 10.1021/acs.inorgchem.5b01825 contributor: fullname: Ghosh, C – volume: 7 start-page: 190 year: 2015 ident: WOS:000347781400001 article-title: Iron-Catalysed Hydrofunctionalisation of Alkenes and Alkynes publication-title: CHEMCATCHEM doi: 10.1002/cctc.201402693 contributor: fullname: Greenhalgh, MD – volume: 24 start-page: 1606 year: 2013 ident: WOS:000330531300002 article-title: Manganese-Mediated C-C Bond Formation via C-H Activation: From Stoichiometry to Catalysis publication-title: SYNLETT doi: 10.1055/s-0033-1339299 contributor: fullname: Wang, CY – start-page: 853 year: 2005 ident: WOS:000228616300001 article-title: Addition of metalloid hydrides to alkynes: Hydrometallation with boron, silicon, and tin publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-2005-861874 contributor: fullname: Trost, BM – volume: 135 start-page: 19107 year: 2013 ident: WOS:000329137300016 article-title: Bis(imino)pyridine Cobalt-Catalyzed Alkene Isomerization-Hydroboration: A Strategy for Remote Hydrofunctionalization with Terminal Selectivity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja4108148 contributor: fullname: Obligacion, JV – volume: 29 start-page: 1811 year: 1988 ident: WOS:A1988N097400019 article-title: ORGANIC-SYNTHESIS USING HALOBORATION REACTIONS .11. A FORMAL CARBOBORATION REACTION OF 1-ALKYNES AND ITS APPLICATION TO THE DISUBSTITUTED AND TRISUBSTITUTED ALKENE SYNTHESIS publication-title: TETRAHEDRON LETTERS contributor: fullname: SATOH, Y – volume: 126 start-page: 13794 year: 2004 ident: WOS:000224685200058 article-title: Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja046753t contributor: fullname: Bart, SC – volume: 308 start-page: 191 year: 2016 ident: WOS:000367412000007 article-title: Manganese organometallic compounds in homogeneous catalysis: Past, present, and prospects publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2015.06.015 contributor: fullname: Valyaev, DA – volume: 2017 start-page: 4344 year: 2017 ident: WOS:000407822200002 article-title: Homogeneous Catalysis by Manganese-Based Pincer Complexes publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201700376 contributor: fullname: Garbe, M – volume: 84 start-page: 7927 year: 2019 ident: WOS:000473116200033 article-title: Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.9b00792 contributor: fullname: Borghs, JC – volume: 55 start-page: 14367 year: 2016 ident: WOS:000387028000030 article-title: Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201607579 contributor: fullname: Zhang, GQ – volume: 10 start-page: 1930 year: 2018 ident: WOS:000431974000002 article-title: From Ruthenium to Iron and ManganeseA Mechanistic View on Challenges and Design Principles of Base-Metal Hydrogenation Catalysts publication-title: CHEMCATCHEM doi: 10.1002/cctc.201701722 contributor: fullname: Zell, T – volume: 43 start-page: 412 year: 2014 ident: WOS:000329070600022 article-title: Selection of boron reagents for Suzuki-Miyaura coupling publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c3cs60197h contributor: fullname: Lennox, AJJ – volume: 8 start-page: 4103 year: 2018 ident: WOS:000431727300043 article-title: Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-Defined Manganese(II) Complex publication-title: ACS CATALYSIS doi: 10.1021/acscatal.8b00983 contributor: fullname: Brzozowska, A – year: 2016 ident: 000535292300006.40 publication-title: Ligand design in metal chemistry: reactivity and catalysis contributor: fullname: Stradiotto, M. – ident: ref13/cit13a doi: 10.1021/ja046753t – ident: ref8/cit8i doi: 10.1002/ejoc.201600018 – ident: ref8/cit8c doi: 10.1055/s-0036-1590818 – ident: ref9/cit9c doi: 10.1002/cctc.201800553 – volume-title: Pincer compounds: chemistry and applications year: 2018 ident: ref10/cit10a contributor: fullname: Morales-Morales D. – ident: ref2/cit2b doi: 10.1021/cr00039a007 – ident: ref9/cit9i doi: 10.1002/cssc.201801660 – ident: ref8/cit8k doi: 10.1055/s-0033-1339299 – ident: ref13/cit13e doi: 10.1039/c3cc46727a – ident: ref13/cit13b doi: 10.1002/cctc.201402693 – ident: ref12/cit12a doi: 10.1002/anie.201704184 – ident: ref6/cit6 doi: 10.1055/s-2005-861874 – ident: ref11/cit11a doi: 10.1002/anie.201805483 – ident: ref4/cit4b doi: 10.1055/s-2004-829165 – ident: ref9/cit9h doi: 10.1002/anie.201810885 – ident: ref12/cit12c doi: 10.1038/s41467-018-06831-9 – ident: ref17/cit17 doi: 10.1021/op2002613 – ident: ref8/cit8e doi: 10.1002/anie.201709010 – ident: ref8/cit8g doi: 10.1039/C7CS00334J – ident: ref13/cit13d doi: 10.1126/science.1214451 – ident: ref8/cit8h doi: 10.1016/j.ccr.2015.06.015 – ident: ref8/cit8f doi: 10.1021/acs.accounts.8b00149 – ident: ref9/cit9b doi: 10.1021/acs.orglett.8b01179 – ident: ref4/cit4a doi: 10.1021/ja00851a038 – ident: ref7/cit7 doi: 10.1021/acs.chemrev.5b00162 – ident: ref9/cit9j doi: 10.1021/acs.orglett.8b03506 – ident: ref14/cit14b doi: 10.1021/jacs.5b00936 – ident: ref13/cit13c doi: 10.1021/ol400990u – ident: ref10/cit10d doi: 10.1039/C7CS00693D – ident: ref5/cit5 doi: 10.1016/S0040-4039(00)82050-X – ident: ref9/cit9g doi: 10.1002/cssc.201802416 – volume: 32 start-page: 1239 year: 2011 ident: ref15/cit15 publication-title: Chem. J. Chin. Univ. contributor: fullname: Fan R.-Q. – ident: ref3/cit3 doi: 10.1021/jo00376a042 – volume-title: Ligand design in metal chemistry: reactivity and catalysis year: 2016 ident: ref10/cit10b doi: 10.1002/9781118839621 contributor: fullname: Stradiotto M. – ident: ref8/cit8a doi: 10.1002/ejoc.201700376 – ident: ref1/cit1 doi: 10.1039/C7GC02006F – ident: ref11/cit11c doi: 10.1021/acs.inorgchem.5b01825 – ident: ref14/cit14a doi: 10.1021/ja4108148 – ident: ref8/cit8b doi: 10.1021/acscatal.8b02869 – ident: ref8/cit8d doi: 10.1002/cctc.201701722 – ident: ref11/cit11d doi: 10.1021/acsomega.7b00713 – ident: ref8/cit8j doi: 10.1021/acscatal.6b00993 – ident: ref2/cit2a doi: 10.1039/C3CS60197H – ident: ref9/cit9a doi: 10.1002/anie.201805630 – ident: ref9/cit9e doi: 10.1002/anie.201704682 – ident: ref11/cit11b doi: 10.1021/ja4116346 – ident: ref4/cit4c doi: 10.1021/jo00038a044 – ident: ref9/cit9f doi: 10.1021/acs.joc.9b00792 – volume-title: Organometallic Pincer Chemistry year: 2014 ident: ref10/cit10c contributor: fullname: Van Koten G. – ident: ref9/cit9d doi: 10.1021/acscatal.8b00983 – ident: ref11/cit11e doi: 10.1021/jacs.7b00879 – ident: ref16/cit16 doi: 10.1021/om0110078 – ident: ref12/cit12b doi: 10.1002/anie.201607579 |
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Snippet | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is... |
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SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst |
URI | http://dx.doi.org/10.1021/acs.orglett.0c00941 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000535292300006 https://www.ncbi.nlm.nih.gov/pubmed/32227972 https://search.proquest.com/docview/2385276128 |
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