Synthetically useful radical reactions mediated by Et
3B are described. An addition of catalytic amount of Et3B to a solution of triphenylstannane, triphenylgermane, or benzenethiol in toluene promotes the effective formation of the corresponding triphenylstannyl, triphenylgermyl, or benzenethiyl radical, respectively. Topics are (1) Et
3B induced radical addition of R3SnH to acetylenes and its application to cyclization reaction, (2) Et
3B induced stereoselective radical addition of Ph
3GeH to acetylenes and its application to isomerization of olefins, (3) Et
3B induced radical addition of thiols to acetylenes, (4) A facile reduction of dithiocarbonates with
n-Bu
3SnH-Et
3B, (5) Et
3B induced hydrodehalogenation of organic halides by tin hydrides, and (6) Et
3B-mediated Reformatsky type reaction and three component coupling reaction of alkyl iodides, methyl vinyl ketone, and carbonyl compounds.
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