PhI(OAc)2-mediated iminobromination for synthesis of bromomethyl cyclic imines starting from alkenyl carbonitriles and Grignard reagents

Stephen Sanjaya; Shunsuke Chiba

doi:10.1016/j.tet.2010.11.060

PhI(OAc)₂-mediated iminobromination for synthesis of bromomethyl cyclic imines starting from alkenyl carbonitriles and Grignard reagents

Stephen Sanjaya, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

10 Citations (Scopus)

Abstract

PhI(OAc)₂-mediated iminobromination was developed starting from alkenyl carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to alkenyl carbonitriles to form N-H imines and their iminohalogenation by subsequent treatment with PhI(OAc)₂.

Original language	English
Pages (from-to)	590-596
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	3
DOIs	https://doi.org/10.1016/j.tet.2010.11.060
Publication status	Published - Jan 21 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Alkenyl carbonitriles
Bromomethyl cyclic imines
Grignard reagents
Iminobromination
PhI(OAc)

Access to Document

10.1016/j.tet.2010.11.060

Cite this

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title = "PhI(OAc)2-mediated iminobromination for synthesis of bromomethyl cyclic imines starting from alkenyl carbonitriles and Grignard reagents",

abstract = "PhI(OAc)2-mediated iminobromination was developed starting from alkenyl carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to alkenyl carbonitriles to form N-H imines and their iminohalogenation by subsequent treatment with PhI(OAc)2.",

keywords = "Alkenyl carbonitriles, Bromomethyl cyclic imines, Grignard reagents, Iminobromination, PhI(OAc)",

author = "Stephen Sanjaya and Shunsuke Chiba",

year = "2011",

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doi = "10.1016/j.tet.2010.11.060",

language = "English",

volume = "67",

pages = "590--596",

journal = "Tetrahedron",

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AU - Sanjaya, Stephen

AU - Chiba, Shunsuke

PY - 2011/1/21

Y1 - 2011/1/21

N2 - PhI(OAc)2-mediated iminobromination was developed starting from alkenyl carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to alkenyl carbonitriles to form N-H imines and their iminohalogenation by subsequent treatment with PhI(OAc)2.

AB - PhI(OAc)2-mediated iminobromination was developed starting from alkenyl carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to alkenyl carbonitriles to form N-H imines and their iminohalogenation by subsequent treatment with PhI(OAc)2.

KW - Alkenyl carbonitriles

KW - Bromomethyl cyclic imines

KW - Grignard reagents

KW - Iminobromination

KW - PhI(OAc)

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DO - 10.1016/j.tet.2010.11.060

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EP - 596

JO - Tetrahedron

JF - Tetrahedron

IS - 3

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