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From Alkenylsilanes to Ketones with Air as the Oxidant
Author(s) -
Kondo Junichi,
Shinokubo Hiroshi,
Oshima Koichiro
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390221
Subject(s) - organosilicon , chemistry , radical , silylation , intermolecular force , tandem , molecular oxygen , oxygen , silanes , organic chemistry , carbon fibers , photochemistry , catalysis , molecule , materials science , silane , composite number , composite material
Air and water are required for a tandem intermolecular radical addition–oxidation sequence that converts alkenylsilanes into a variety of ketones. The reaction of 2‐silyl‐1‐alkenes with various carbon‐centered radicals (see scheme) provides carbonyl compounds in good yields. This process represents a novel oxidative transformation of organosilicon compounds with molecular oxygen as the oxidant. R 3 Si=MePh 2 Si, Me 2 PhSi, R 1 =Me, Ph, CO 2 Me, SiMe 2 Ph, R 2 =CH 2 COR′ (R′=OBn, NEt 2 , O n Bu, Ph), C 6 F 13 .