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Nickel‐Catalyzed, Directing‐Group‐Assisted [2+2+2] Cycloaddition of Imine and Alkynes
Author(s) -
Adak Laksmikanta,
Chan Wei Chuen,
Yoshikai Naohiko
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000564
Subject(s) - alkyne , imine , cycloaddition , chemistry , aldimine , catalysis , medicinal chemistry , oxidative addition , reductive elimination , combinatorial chemistry , nickel , yield (engineering) , organic chemistry , materials science , metallurgy
An aldimine bearing a 3‐methyl‐2‐pyridyl group undergoes [2+2+2] cycloaddition reaction with two alkyne molecules under nickel catalysis to afford a 1,2‐dihydropyridine derivative in moderate to good yield. The reaction is likely to involve oxidative cyclization of the imine and alkyne, insertion of another alkyne, and CN reductive elimination, followed by a 1,5‐sigmatropic hydrogen shift. The pyridyl group is proposed to facilitate the reaction by chelation to the aza‐nickelacycle intermediates.