Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 39, Pages 16926-16932Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202006317
Keywords
alkynylation; asymmetric radical reactions; copper; decarboxylation; photocatalysis
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Funding
- National Natural Science Foundation of China [21722203, 21831002, 21801116]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Guangdong Innovative Program [2019BT02Y335]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
- SUSTech Special Fund for the Construction of High-Level Universities [G02216303]
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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.
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