Carboxylic acid-assisted sterically demanding reductive cross-coupling between cycloalkenyl and alkyl bromides

A nickel-catalysed reductive cross-coupling reaction between 2-bromo cycloalkenyl carboxylic acids and alkyl bromides has been developed, affording all-carbon tetrasubstituted cycloalkenes in moderate to excellent yields up to 92%. Mechanistic studies indicated that the carboxylic acid group plays a...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 8; pp. 1897 - 1902
Main Authors An, Jinglin, Zhou, Xue, Zhang, Yifan, Ye, Zhenfei, Guo, Qianyou, Song, Hao, Song, Zhenlei, Liu, Xiao-Yu, Qin, Yong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.04.2023
Royal Society of Chemistry
Subjects
Bromides
Carbon cycle
Carboxylic acids
Chemical reactions
Chemistry
Chemistry, Organic
Cross coupling
Nickel
Organic chemistry
Organic compounds
Physical Sciences
Science & Technology
HALIDES
VINYL
NICKEL
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Summary:A nickel-catalysed reductive cross-coupling reaction between 2-bromo cycloalkenyl carboxylic acids and alkyl bromides has been developed, affording all-carbon tetrasubstituted cycloalkenes in moderate to excellent yields up to 92%. Mechanistic studies indicated that the carboxylic acid group plays an important assisting role in this sterically demanding coupling reaction.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d3qo00155e