Silver-catalyzed oxidative alkylation/alkynylation of 1,4-enynyl-3-ols with alkylbromides through radical 1,2-alkynyl migration

De Chen; Nianqi Zhang; Qiuju Liang; Wei Deng; Zhiyi Xiao; Wanrong Dong; Jiannan Xiang

Catalysis Communications (Jan 2024)

Silver-catalyzed oxidative alkylation/alkynylation of 1,4-enynyl-3-ols with alkylbromides through radical 1,2-alkynyl migration

De Chen,
Nianqi Zhang,
Qiuju Liang,
Wei Deng,
Zhiyi Xiao,
Wanrong Dong,
Jiannan Xiang

Affiliations

De Chen: College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan Province 410082, PR China
Nianqi Zhang: College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan Province 410082, PR China
Qiuju Liang: Hunan Engineering Technology Center of Photographic Materials(2022TP2027), Wujo High-Tech Materials CO. LTD, Loudi City, Hunan Province 417000, PR China; Technology Center of China Tobacco Hunan Industrial Co. Ltd, Laodong Mid Rd. 426, Changsha, Hunan Province 410014, PR China
Wei Deng: College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan Province 410082, PR China
Zhiyi Xiao: Hunan Engineering Technology Center of Photographic Materials(2022TP2027), Wujo High-Tech Materials CO. LTD, Loudi City, Hunan Province 417000, PR China; Corresponding authors.
Wanrong Dong: College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan Province 410082, PR China; Corresponding authors.
Jiannan Xiang: College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, Hunan Province 410082, PR China; Corresponding authors.

Journal volume & issue: Vol. 186
p. 106824

Abstract

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In this study, we have described a novel reaction between 1,4-enynyl-3-ols and alkyl bromides. The reaction was carried out in the presence of Ag2O, following a free radical 1,2-alkynyl migration pathway, which was confirmed through control experiments. This methodology offers several advantages, including high efficiency and a wide range of applicable substrates.

Published in Catalysis Communications

ISSN: 1566-7367 (Print); 1873-3905 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: https://www.journals.elsevier.com/catalysis-communications

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