Issue 9, 2016

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

Abstract

A nickel-catalyzed regioselective addition/cyclization of o-(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 anti-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.

Graphical abstract: Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Mar 2016
Accepted
19 May 2016
First published
19 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 5815-5820

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

X. Zhang, X. Xie and Y. Liu, Chem. Sci., 2016, 7, 5815 DOI: 10.1039/C6SC01191H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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