Direct β- and γ-C(sp3)-H Alkynylation of Free Carboxylic Acids

被引：51

作者：

Ghiringhelli, Francesca ^{[1
]}

Uttry, Alexander ^{[1
]}

Ghosh, Kiron Kumar ^{[1
]}

Van Gemmeren, Manuel ^{[1
]}

机构：

[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 36, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 51期

关键词：

Alkynylation; Carboxylic acids; C-H activation; Ligand-enabled catalysis; Palladium; C-H BONDS; CATALYZED DIRECT ETHYNYLATION; ALPHA-AMINO-ACIDS; C(SP(3))-H BONDS; BETA-C(SP(3))-H ARYLATION; DERIVATIVES; SP(3); FUNCTIONALIZATIONS; ACTIVATION; SP(2);

D O I：

10.1002/anie.202010784

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this study we report the identification of a novel class of ligands for palladium-catalyzed C(sp(3))-H activation that enables the direct alkynylation of free carboxylic acid substrates. In contrast to previous synthetic methods, no introduction/removal of an exogenous directing group is required. A broad scope of acids including both alpha-quaternary and challenging alpha-non-quaternary can be used as substrates. Additionally, the alkynylation in the distal gamma-position is reported. Finally, this study encompasses preliminary findings on an enantioselective variant of the title transformation as well as synthetic applications of the products obtained.

引用

页码：23127 / 23131

页数：5

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