Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene–Ynes and Bis-Allenes

The carbocyanative cyclization of allene–ynes and bis-allenes under nickel catalysis is described. The key steps are the regioselective hydronickelation of allenes and subsequent cyclization via carbometalation. The former step determines the reaction pathway, and the latter controls the stereochemi...

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Published in:Journal of organic chemistry 2013-11, Vol.78 (21), p.10763-10775
Main Authors: Amako, Yuka, Hori, Hiroto, Arai, Shigeru, Nishida, Atsushi
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Alkenes - chemistry
Catalysis
Cyclization
Molecular Structure
Nickel - chemistry
Palladium - chemistry
Stereoisomerism
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description The carbocyanative cyclization of allene–ynes and bis-allenes under nickel catalysis is described. The key steps are the regioselective hydronickelation of allenes and subsequent cyclization via carbometalation. The former step determines the reaction pathway, and the latter controls the stereochemistry of substituted olefins. The products are useful carbo- and heterocycles that include a cyano group, functionalized double bonds, and quaternary carbons.
doi_str_mv 10.1021/jo401758v
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alkadienes - chemistry
Alkenes - chemistry
Catalysis
Cyclization
Molecular Structure
Nickel - chemistry
Palladium - chemistry
Stereoisomerism
title Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene–Ynes and Bis-Allenes
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