Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

Chun Law Man; Wai Cheung Tin; Kwok Yin Wong; Hang Chan Tak

doi:10.1021/jo062198x

Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

Chun Law Man, Wai Cheung Tin, Kwok Yin Wong, Hang Chan Tak

Research output: Journal article publication › Journal article › Academic research › peer-review

52 Citations (Scopus)

Abstract

(Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.

Original language	English
Pages (from-to)	923-929
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	72
Issue number	3
DOIs	https://doi.org/10.1021/jo062198x
Publication status	Published - 2 Feb 2007

ASJC Scopus subject areas

Organic Chemistry

More information

10.1021/jo062198x

Cite this

@article{0ce6b2135adf4e9c839388dd251e66cc,

title = "Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids",

abstract = "(Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.",

author = "Man, {Chun Law} and Tin, {Wai Cheung} and Wong, {Kwok Yin} and Tak, {Hang Chan}",

year = "2007",

month = feb,

day = "2",

doi = "10.1021/jo062198x",

language = "English",

volume = "72",

pages = "923--929",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

AU - Man, Chun Law

AU - Tin, Wai Cheung

AU - Wong, Kwok Yin

AU - Tak, Hang Chan

PY - 2007/2/2

Y1 - 2007/2/2

N2 - (Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.

AB - (Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.

UR - http://www.scopus.com/inward/record.url?scp=33846906499&partnerID=8YFLogxK

U2 - 10.1021/jo062198x

DO - 10.1021/jo062198x

M3 - Journal article

C2 - 17253812

SN - 0022-3263

VL - 72

SP - 923

EP - 929

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

Abstract

ASJC Scopus subject areas

More information

Other files and links

Fingerprint

Cite this