Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters

Ke Ni; Ling-Guo Meng; Hongjie Ruan; Lei Wang

doi:10.1039/C9CC04090K

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Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters†

Ke Ni,^a Ling-Guo Meng,*^a Hongjie Ruan^a and Lei Wang

*^ab

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* Corresponding authors

^a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
E-mail: milig@126.com, leiwang@chnu.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N₂ or O₂). A N₂ atmosphere favours propargyl alcohols via a direct C–C coupling process, whereas an O₂ atmosphere results in the generation of α-ketoesters through the oxidative C [triple bond, length as m-dash] C/C–O coupling pathway.

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Article information

DOI: https://doi.org/10.1039/C9CC04090K
Article type: Communication
Submitted: 27 May 2019
Accepted: 21 Jun 2019
First published: 21 Jun 2019

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Chem. Commun., 2019,55, 8438-8441

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Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters

K. Ni, L. Meng, H. Ruan and L. Wang, Chem. Commun., 2019, 55, 8438 DOI: 10.1039/C9CC04090K

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Chemical Communications

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters†

Abstract

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Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters

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