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Iron‐Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides
Author(s) -
Ilies Laurean,
Ichikawa Saki,
Asako Sobi,
Matsubara Tatsuaki,
Nakamura Eiichi
Publication year - 2015
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.201500276
Subject(s) - chemistry , alkylation , halide , reagent , catalysis , denticity , medicinal chemistry , primary (astronomy) , organic chemistry , combinatorial chemistry , metal , physics , astronomy
Alkenes and arenes possessing a bidentate directing group are alkylated with a primary or secondary alkylzinc halide in the presence of an iron/diphosphine catalyst and a dichloroalkane oxidant. Acrylamides, including unsubstituted and monosubstituted ones, react stereoselectively. Under these reaction conditions, β‐hydrogen elimination and homocoupling of the organometallic reagent are largely suppressed. The reaction may proceed through CH activation catalyzed by an organoiron(III) species.