Regioselectively switchable alkyne cyclotrimerization catalyzed by a Ni(ii)/bidentate P-ligand/Zn system with ZnI2 as an additive

A simple catalytic system of Ni(PPh3)2Cl2/dppb or dppm/Zn can effect an efficient and regioselectively controlled alkyne cyclotrimerization to form 1,2,4- (with no additive) or 1,3,5-regioisomers (with the use of a ZnI2 additive). This protocol features the advantages of facile manipulation, mild co...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (9), p.2357-2367
Main Authors: Jiang-Tao, Fan, Xin-Heng, Fan, Cai-Yan, Gao, Wei, Jinchao, Lian-Ming, Yang
Format: Article
Language:English
Subjects:
Alkynes
Benzene
Organic chemistry
Regioselectivity
Substrates
Zinc
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Summary:A simple catalytic system of Ni(PPh3)2Cl2/dppb or dppm/Zn can effect an efficient and regioselectively controlled alkyne cyclotrimerization to form 1,2,4- (with no additive) or 1,3,5-regioisomers (with the use of a ZnI2 additive). This protocol features the advantages of facile manipulation, mild conditions, broad substrate scope, high yields, excellent functional-group tolerance and easily controllable regioselectivity, and demonstrates practical potential for the construction of complicated and well-defined poly-substituted benzene derivatives. The mechanistic studies were carried out preliminarily.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01913a