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镍催化炔腈与有机硼酸的环化反应，涉及炔烃的碳金属化反应

Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving -carbometalation of alkynes.

作者信息

Zhang Xingjie, Xie Xin, Liu Yuanhong

机构信息

State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China . Email:

出版信息

Chem Sci. 2016 Sep 1;7(9):5815-5820. doi: 10.1039/c6sc01191h. Epub 2016 May 19.

DOI:10.1039/c6sc01191h
PMID:30034720
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6021782/
Abstract

A nickel-catalyzed regioselective addition/cyclization of -(cyano)phenyl propargyl ethers with arylboronic acids has been developed, which provides an efficient protocol for the synthesis of highly functionalized 1-naphthylamines with wide structural diversity. The reaction is characterized by a regioselective and -addition of the arylboronic acids to the alkyne and subsequent facile nucleophilic addition of the resulting alkenylmetal to the tethered cyano group. Mechanistic studies reveal that a Ni(i) species might be involved in the catalytic process.

摘要

已开发出一种镍催化的（氰基）苯基炔丙基醚与芳基硼酸的区域选择性加成/环化反应，该反应为合成具有广泛结构多样性的高度官能化1-萘胺提供了一种有效方法。该反应的特点是芳基硼酸对炔烃进行区域选择性的β-加成，随后生成的烯基金属对相连的氰基进行亲核加成。机理研究表明，催化过程中可能涉及Ni(i)物种。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/9e7f221810f7/c6sc01191h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/74ea68b17b3a/c6sc01191h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/02b071f38feb/c6sc01191h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/9e7f221810f7/c6sc01191h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/74ea68b17b3a/c6sc01191h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/02b071f38feb/c6sc01191h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7246/6021782/9e7f221810f7/c6sc01191h-s3.jpg

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