Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides

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

doi:10.1021/ja5066015

Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides

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

Graduate School of Natural Science and Technology

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

140 Citations (Scopus)

Abstract

Alkenes, arenes, and heteroarenes possessing an 8-quinolylamide group as the directing group are alkylated with primary and secondary alkyl tosylates, mesylate, and halides in the presence of Fe(acac) ₃/ diphosphine as a catalyst and ArZnBr as a base. The reaction proceeds stereospeci fically for alkene substrates and takes place without loss of regiochemical integrity of the starting secondary tosylate, but with loss of the stereochemistry of the chiral center.

Original language	English
Pages (from-to)	13126-13129
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	38
DOIs	https://doi.org/10.1021/ja5066015
Publication status	Published - Sept 24 2014

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides",

abstract = "Alkenes, arenes, and heteroarenes possessing an 8-quinolylamide group as the directing group are alkylated with primary and secondary alkyl tosylates, mesylate, and halides in the presence of Fe(acac) 3/ diphosphine as a catalyst and ArZnBr as a base. The reaction proceeds stereospeci fically for alkene substrates and takes place without loss of regiochemical integrity of the starting secondary tosylate, but with loss of the stereochemistry of the chiral center.",

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

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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T1 - Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides

AU - Ilies, Laurean

AU - Matsubara, Tatsuaki

AU - Ichikawa, Saki

AU - Asako, Sobi

AU - Nakamura, Eiichi

PY - 2014/9/24

Y1 - 2014/9/24

N2 - Alkenes, arenes, and heteroarenes possessing an 8-quinolylamide group as the directing group are alkylated with primary and secondary alkyl tosylates, mesylate, and halides in the presence of Fe(acac) 3/ diphosphine as a catalyst and ArZnBr as a base. The reaction proceeds stereospeci fically for alkene substrates and takes place without loss of regiochemical integrity of the starting secondary tosylate, but with loss of the stereochemistry of the chiral center.

AB - Alkenes, arenes, and heteroarenes possessing an 8-quinolylamide group as the directing group are alkylated with primary and secondary alkyl tosylates, mesylate, and halides in the presence of Fe(acac) 3/ diphosphine as a catalyst and ArZnBr as a base. The reaction proceeds stereospeci fically for alkene substrates and takes place without loss of regiochemical integrity of the starting secondary tosylate, but with loss of the stereochemistry of the chiral center.

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U2 - 10.1021/ja5066015

DO - 10.1021/ja5066015

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SP - 13126

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 38

ER -

Iron-catalyzed directed alkylation of aromatic and olefinic carboxamides with primary and secondary alkyl tosylates, mesylates, and halides

Abstract

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