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Decarboxylative Alkynylation
Author(s) -
Smith Joel M.,
Qin Tian,
Merchant Rohan R.,
Edwards Jacob T.,
Malins Lara R.,
Liu Zhiqing,
Che Guanda,
Shen Zichao,
Shaw Scott A.,
Eastgate Martin D.,
Baran Phil S.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705107
Subject(s) - alkyne , alkynylation , combinatorial chemistry , chemistry , catalysis , scope (computer science) , decarboxylation , scalability , carboxylic acid , reaction conditions , organic chemistry , computer science , programming language , database
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 in situ 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.