Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides

Laurean Ilies; Saki Ichikawa; Sobi Asako; Tatsuaki Matsubara; Eiichi Nakamura

doi:10.1002/adsc.201500276

Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides

Laurean Ilies, Saki Ichikawa, Sobi Asako, Tatsuaki Matsubara, Eiichi Nakamura

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

Abstract

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 C-H activation catalyzed by an organoiron(III) species.

Original language	English
Pages (from-to)	2175-2179
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	10
DOIs	https://doi.org/10.1002/adsc.201500276
Publication status	Published - Jul 1 2015

Keywords

C-H activation
alkylation
amides
iron
zinc

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201500276

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abstract = "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 C-H activation catalyzed by an organoiron(III) species.",

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author = "Laurean Ilies and Saki Ichikawa and Sobi Asako and Tatsuaki Matsubara and Eiichi Nakamura",

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T1 - Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides

AU - Ilies, Laurean

AU - Ichikawa, Saki

AU - Asako, Sobi

AU - Matsubara, Tatsuaki

AU - Nakamura, Eiichi

PY - 2015/7/1

Y1 - 2015/7/1

N2 - 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 C-H activation catalyzed by an organoiron(III) species.

AB - 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 C-H activation catalyzed by an organoiron(III) species.

KW - C-H activation

KW - alkylation

KW - amides

KW - iron

KW - zinc

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 10

ER -

Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides

Abstract

Keywords

ASJC Scopus subject areas

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