Tetrahedron p. 1017 - 1026 (1999)
Update date:2022-09-26
Topics: Catalyst Product Formation Chemoselectivity Reductive Conditions Introduction of Aromatic Compounds Choice of Carbonyl Reagents
Miyai, Takashi
Onishi, Yoshiyuki
Baba, Akio
Reductive Friedel-Crafts alkylation of aromatics with ketones or aldehydes was characteristically catalyzed by indium compounds in preference to general catalysts like AlCl3 and BF3, where hydrosilanes would play an important role both as a hydride donor and as a co-catalyst. Chemoselective utilization of ketone moieties as alkylating reagents took place even in the presence of halogen, ester or ether moieties which are very susceptible under traditional Friedel-Crafts conditions. Discussion on a plausible intermediate was carried out by some controlled experiments.
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