Base-promoted direct E-selective olefination of organoammonium salts with sulfones toward stilbenes and conjugated 1,3-dienes

Abstract

A base-promoted direct deaminative olefination of organoammonium salts was developed. Only mediated by KOtBu, a series of benzyl and cinnamyl ammonium salts were reacted smoothly with sulfones, producing the valuable...

Recent advances in synthesis of stilbene derivativesviacross-coupling reaction

“…Another base-mediated direct deaminative olefination of benzyl 40a and cinnamyl 41a ammonium salts with various sulfones 40b and 41b giving access to trans -stilbenes 40c and conjugated 1,3-dienes 41c was reported by the Chen group (Scheme 48). 61 Using this method, resveratrol and DMU-212 were also successfully obtained.…”

Synthesis of Stilbenes by Cyanide/Base-Mediated Coupling of Benzylic Chlorides and Alcohols

“…Benzylic sulfones can form the diarylethene motif when reacted with benzylic alcohols in the presence of a nickel catalyst and a base 5 or with benzylic quaternary ammonium salts and a base. 6 Two benzaldehydes can undergo reductive coupling with either MesP(TMS)Li 7 or B2Pin2 8 while a rhodium complex catalyzes the direct aerobic alkenylation of aromatic compounds with styrenes. 9 Visible light can be used to mediate the coupling of -nitrostyrenes and arylazo sulfones 10 as well as the coupling of -styrylboronic acids and arenediazonium salts.…”

“…1 H NMR (400 MHz, CDCl 3 ):  = 7.54-7.49 (m, 2 H), 7.36 (t, J = 7.7 Hz, 2 H), 7.31 (s, 1 H), 7.30-7.22 (m, 2 H), 7.14 (d, J = 7. 6 Hz, 1 H), 7.08 (s, 2 H), 2.31 (s, 3 H), 2.29 (s, 3 H). 13 C NMR (101 MHz, CDCl 3 ):  = 137.7, 136.9, 136.4, 135.1, 130.1, 128.9, 128.8, 127.9, 127.7, 127.5, 126.5, 124.2, 20.0, 19.7.…”