Decarboxylative Alkynylation

被引：123

作者：

Smith, Joel M. ^{[1
]}

Qin, Tian ^{[1
]}

Merchant, Rohan R. ^{[1
]}

Edwards, Jacob T. ^{[1
]}

Malins, Lara R. ^{[1
]}

Liu, Zhiqing ^{[2
]}

Che, Guanda ^{[2
]}

Shen, Zichao ^{[2
]}

Shaw, Scott A. ^{[3
]}

Eastgate, Martin D. ^{[4
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, North Torrey Pines Rd, La Jolla, CA 92037 USA

[2] Asymchem Labs Tianjin Co Ltd, TEDA, Tianjin 300457, Peoples R China

[3] Bristol Myers Squibb, Discovery Chem, 350 Carter Rd, Hopewell, NJ 08540 USA

[4] Bristol Myers Squibb, Chem Dev, One Squibb Dr, New Brunswick, NJ 08903 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 39期

关键词：

alkynylation; homologation; iron catalysis; nickel catalysis; redox-active esters; REDOX-ACTIVE ESTERS; SECONDARY ALKYL-HALIDES; CARBOXYLIC-ACIDS; COUPLING REACTIONS; MILD;

D O I：

10.1002/anie.201705107

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a new decarboxylative cross-coupling method that affords terminal and substituted alkynes from various carboxylic acids is described using both nickel- and iron-based catalysts. The use of N-hydroxytetrachlorophthalimide (TCNHPI) esters is crucial to the success of the transformation, and the reaction is amenable to insitu carboxylic acid activation. Additionally, an inexpensive, commercially available alkyne source is employed in this formal homologation process that serves as a surrogate for other well-established alkyne syntheses. The reaction is operationally simple and broad in scope while providing succinct and scalable avenues to previously reported synthetic intermediates.

引用

页码：11906 / 11910

页数：5

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