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Pd‐Catalyzed Regioselective Olefination of N ‐Tosylhydrazones with Benzyl Bromides
Author(s) -
Sun Zhenze,
He Jing,
Li Weiwei,
Li Xuezhen,
Feng Yijiao,
Liu Yan,
Liu Ping,
Han Sheng
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002010
Subject(s) - regioselectivity , chemistry , catalysis , olefin fiber , bromide , substrate (aquarium) , palladium , medicinal chemistry , functional group , combinatorial chemistry , organic chemistry , oceanography , polymer , geology
A palladium‐catalyzed regioselective olefination of cycloalkylphenylmethylene N ‐tosylhydrazones and benzyl bromide was developed. A series of E ‐type tri‐substituted olefin compounds were obtained in 43–95% through the highly selective β ‐H elimination. The results showed that the β ‐H at the benzyl position took precedence over the β ‐H at the cycloalkyl position for the alkylpalladium intermediate, avoiding the formation of tetra‐substituted olefins. High regioselectivity, wide substrate scope, and good functional group tolerance are the advantages of this reaction.