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Regioselective [2+2+2] Cycloaddition Reaction Using Allene‐ynes with Simple Allenes under Nickel Catalysis
Author(s) -
Arai Shigeru,
Izaki Arisa,
Amako Yuka,
Nakajima Masaya,
Uchiyama Masanobu,
Nishida Atsushi
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900719
Subject(s) - allene , chemistry , regioselectivity , cycloaddition , stereoselectivity , substituent , catalysis , substrate (aquarium) , nickel , computational chemistry , stereochemistry , organic chemistry , oceanography , geology
A Ni‐catalyzed [2+2+2] cycloaddition reaction between allene‐ynes and various mono‐, di‐ and tri‐substituted allenes is described. This protocol effectively differentiates allenyl π components and shows broad substrate generality to give highly functionalized carbocycles. A DFT study played a key role in revealing a detailed reaction mechanism that controls site‐, regio‐ and stereoselectivity, which are thought to originate in the substituent effect on π‐bonds in the early transition state.