Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
- 21 September 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 59 (39), 16926-16932
- https://doi.org/10.1002/anie.202006317
Abstract
We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp(3))-C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.Funding Information
- National Natural Science Foundation of China (21722203, 21831002, 21801116)
This publication has 88 references indexed in Scilit:
- Silver-Catalyzed Decarboxylative Alkynylation of Aliphatic Carboxylic Acids in Aqueous SolutionJournal of the American Chemical Society, 2012
- Palladium‐Catalyzed Cross‐Coupling: A Historical Contextual Perspective to the 2010 Nobel PrizeAngewandte Chemie-International Edition, 2012
- Palladiumkatalysierte Kreuzkupplungen: eine historische Perspektive im Kontext der Nobel‐Preise 2010Angewandte Chemie, 2012
- Enantioselective Synthesis of a GPR40 Agonist AMG 837 via Catalytic Asymmetric Conjugate Addition of Terminal Alkyne to α,β-Unsaturated ThioamideOrganic Letters, 2011
- Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from IodoresorcinolsOrganic Process Research & Development, 2009
- The Copper‐Catalyzed Decarboxylative Coupling of the sp3‐Hybridized Carbon Atoms of α‐Amino AcidsAngewandte Chemie, 2009
- The Copper‐Catalyzed Decarboxylative Coupling of the sp3‐Hybridized Carbon Atoms of α‐Amino AcidsAngewandte Chemie, 2009
- Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group TransformationsAccounts of Chemical Research, 2008
- Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic HalidesJournal of the American Chemical Society, 2005
- Reductive coupling reaction of benzyl, allyl and alkyl halides in aqueous medium promoted by zincJournal of the Brazilian Chemical Society, 2003