Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes

Daria Kurandina; Vladimir Gevorgyan

doi:10.1021/acs.orglett.6b00541

Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes

Daria Kurandina, Vladimir Gevorgyan

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

73 Scopus citations

Abstract

The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.

Original language	English (US)
Pages (from-to)	1804-1807
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.6b00541
State	Published - Apr 15 2016
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00541

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abstract = "The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.",

author = "Daria Kurandina and Vladimir Gevorgyan",

note = "Funding Information: We thank National Science Foundation (CHE-1362541) for financial support of this work. We also thank Dr. Olga Zatolochnaya for initial experiments and fruitful discussions. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Kurandina, Daria

AU - Gevorgyan, Vladimir

N1 - Funding Information: We thank National Science Foundation (CHE-1362541) for financial support of this work. We also thank Dr. Olga Zatolochnaya for initial experiments and fruitful discussions. Publisher Copyright: © 2016 American Chemical Society.

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N2 - The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.

AB - The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.

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Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes

Abstract

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