Synthesis of trans-stilbenes via phosphine-catalyzed coupling reactions of benzylic halides

Abstract

An efficient and practical phosphine−catalyzed homo−coupling reaction of benzyl chlorides is described. The reactions proceed smoothly in the presence of CsF/B(OMe)3 and NaH as the base, respectively, to provide trans-stilbenes...

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

“…Transition metal-free formation of E -selective stilbenes 42b using phosphine catalyst in the homo-coupling reaction of benzylic halides 42a , with NaH and CsF used as the bases, was reported by Bao et al (Scheme 49). 62 In this method, unsymmetrical stilbenes were also obtained from the reaction of benzyl chlorides 42a with phosphonium salts A . Phenylcarbene E and phosphonium alkoxide B were key intermediates in the reaction mechanism (Scheme 50).…”