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Characterization of the Nucleophilic Allylindium Species Generated from Allyl Bromide and Indium(0) in Aqueous Media
Author(s) -
Yasuda Makoto,
Haga Masahiko,
Nagaoka Yasunori,
Baba Akio
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000956
Subject(s) - chemistry , nucleophile , allyl bromide , bromide , indium , benzaldehyde , medicinal chemistry , aqueous solution , pyridine , aqueous medium , organic chemistry , catalysis
The reductive system of allyl bromide and indium(0) in water generated monoallylindium(III) dibromide and diallylindium(III) bromide. These compounds were characterized by X‐ray analysis after complexation with 3,5‐dibromopyridine or 4‐(dimethylamino)pyridine, respectively. Both isolated complexes showed high nucleophilicity and reacted with benzaldehyde to give the allylation product. The diallylindium(III) bromide was less stable in water than the monoallylindium(III) dibromide. The reaction of the diallylindium(III) with benzhydrol gave a (μ‐alkoxido)indium species that showed nucleophilicity. This result suggests that allyl(μ‐hydroxido)indium also acted as a nucleophile in an aqueous Barbie‐type reaction system.