Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles

The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have b...

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Published in:Organic & biomolecular chemistry 2024-10, Vol.22 (41), p.8268-8272
Main Authors: Song, Lei, Li, Fu-Qiang, Qiu, Xiao-Han, Wei, Guo-Zhen, Chen, Hui-Yu, Bian, Ming, Gao, Yu-Ning, Liu, Zhen-Jiang
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Language:English
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Copper
Indoles
Thiols
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container_end_page 8272
container_issue 41
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container_title Organic & biomolecular chemistry
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creator Song, Lei
Li, Fu-Qiang
Qiu, Xiao-Han
Wei, Guo-Zhen
Chen, Hui-Yu
Bian, Ming
Gao, Yu-Ning
Liu, Zhen-Jiang
description The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained. This methodology offers significant advantages including mild reaction conditions, cheap catalysts, good yields and broad substrate compatibility. The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed, involving a rarely studied α-addition process to a copper-allenylidene intermediate.
doi_str_mv 10.1039/d4ob01164c
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source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Copper
Indoles
Thiols
title Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles
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