Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans

Zhonghua Xia; Omar Khaled; Virginie Mouriès-Mansuy; Cyril Ollivier; Louis Fensterbank

doi:10.1021/acs.joc.6b01060

Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans

Zhonghua Xia, Omar Khaled, Virginie Mouriès-Mansuy, Cyril Ollivier^*, Louis Fensterbank

^*Corresponding author for this work

Sorbonne Université

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

95 Citations (Scopus)

Abstract

A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient approach to benzofuran derivatives. The scope of the transformation is wide, and the limitations are discussed. The reaction is proposed to proceed through a photoredox-promoted generation of a vinylgold(III) intermediate that undergoes reductive elimination to provide the heterocyclic coupling adduct.

Original language	English
Pages (from-to)	7182-7190
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	81
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.6b01060
Publication status	Published - 19 Aug 2016
Externally published	Yes

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Xia, Z., Khaled, O., Mouriès-Mansuy, V., Ollivier, C., & Fensterbank, L. (2016). Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans. Journal of Organic Chemistry, 81(16), 7182-7190. https://doi.org/10.1021/acs.joc.6b01060

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abstract = "A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient approach to benzofuran derivatives. The scope of the transformation is wide, and the limitations are discussed. The reaction is proposed to proceed through a photoredox-promoted generation of a vinylgold(III) intermediate that undergoes reductive elimination to provide the heterocyclic coupling adduct.",

author = "Zhonghua Xia and Omar Khaled and Virginie Mouri{\`e}s-Mansuy and Cyril Ollivier and Louis Fensterbank",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.6b01060",

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AU - Khaled, Omar

AU - Mouriès-Mansuy, Virginie

AU - Ollivier, Cyril

AU - Fensterbank, Louis

PY - 2016/8/19

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Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans

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