Decarboxylative Alkynylation

Joel M. Smith; Tian Qin; Rohan R. Merchant; Jacob T. Edwards; Lara R. Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A. Shaw; Martin D. Eastgate; Phil S. Baran

doi:10.1002/anie.201705107

Decarboxylative Alkynylation

Joel M. Smith, Tian Qin, Rohan R. Merchant, Jacob T. Edwards, Lara R. Malins, Zhiqing Liu, Guanda Che, Zichao Shen, Scott A. Shaw, Martin D. Eastgate, Phil S. Baran

Research output: Contribution to journal › Article › peer-review

124 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	11906-11910
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	39
DOIs	https://doi.org/10.1002/anie.201705107
State	Published - Sep 18 2017
Externally published	Yes

Keywords

alkynylation
homologation
iron catalysis
nickel catalysis
redox-active esters

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201705107

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abstract = "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.",

keywords = "alkynylation, homologation, iron catalysis, nickel catalysis, redox-active esters",

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doi = "10.1002/anie.201705107",

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T1 - Decarboxylative Alkynylation

AU - Smith, Joel M.

AU - Qin, Tian

AU - Merchant, Rohan R.

AU - Edwards, Jacob T.

AU - Malins, Lara R.

AU - Liu, Zhiqing

AU - Che, Guanda

AU - Shen, Zichao

AU - Shaw, Scott A.

AU - Eastgate, Martin D.

AU - Baran, Phil S.

PY - 2017/9/18

Y1 - 2017/9/18

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AB - 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.

KW - alkynylation

KW - homologation

KW - iron catalysis

KW - nickel catalysis

KW - redox-active esters

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Decarboxylative Alkynylation

Abstract

Keywords

ASJC Scopus subject areas

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