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钯催化的伯醇碳-碳键裂解：炔醛与卤代芳烃的脱羰偶联反应

Palladium-catalyzed carbon-carbon bond cleavage of primary alcohols: decarbonylative coupling of acetylenic aldehydes with haloarenes.

作者信息

Jin Zewei, Li Qiang, Zhu Maoshuai, Zhang Yanqiong, Yan Xufei, Zhou Xiangge

机构信息

College of Chemistry, Sichuan University 29 Wangjiang Road Chengdu 610064 P. R. China

West China School of Public Health and West China Fourth Hospital, Sichuan University Chengdu 610041 P. R. China

出版信息

RSC Adv. 2025 Mar 11;15(10):7826-7831. doi: 10.1039/d5ra00357a. eCollection 2025 Mar 6.

DOI:10.1039/d5ra00357a
PMID:40070398
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11895861/
Abstract

In the current work, a palladium-catalyzed C-C bond cleavage reaction of primary alcohols has been developed. This transformation was characterized by a broad substrate scope, superior functional group tolerance, and high efficiency for selective C-C bond cleavage and was then followed by alkynyl-aryl cross coupling. Mechanism studies indicated that the propargyl alcohols underwent β-H elimination to form aldehydes rather than having undergone β-C elimination. The corresponding aldehyde intermediates then proceeded through a decarbonylation and coupling reaction with haloarenes to yield diarylacetylenes.

摘要

在当前的工作中，已经开发出一种钯催化的伯醇碳-碳键裂解反应。这种转化具有底物范围广、官能团耐受性好以及选择性碳-碳键裂解效率高的特点，随后进行炔基-芳基交叉偶联。机理研究表明，炔丙醇经历β-H消除形成醛，而不是β-C消除。相应的醛中间体随后通过脱羰反应与卤代芳烃发生偶联反应，生成二芳基乙炔。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/37e50a430fa6/d5ra00357a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/d12a97d2a604/d5ra00357a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/dbc565764560/d5ra00357a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/005291425e17/d5ra00357a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/650b72e40fdd/d5ra00357a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/097b3067052c/d5ra00357a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/37e50a430fa6/d5ra00357a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/d12a97d2a604/d5ra00357a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/dbc565764560/d5ra00357a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/005291425e17/d5ra00357a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/650b72e40fdd/d5ra00357a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/097b3067052c/d5ra00357a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e93/11895861/37e50a430fa6/d5ra00357a-s6.jpg

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本文引用的文献

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