Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1E,3E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

Abstract

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Unsymmetrically Substituted Stilbene–Maleic‐Anhydride Copolymers: Improving Synthesis and Measuring Substituent Effects on Conversion

“…[Lit. 133−136 °C] [ 22 ] ; 1 H NMR (CDCl 3 , 400 MHz) δ ppm: 7.46 (m, 4H), 7.33 (m, 2H), 7.23 (m, 1H), 7.06 (d, 1H, J app = 16.3 Hz), 6.96 (d, 1H, J app = 16.3 Hz), 6.89 (m, 2H), 3.82 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ ppm: 159.3, 137.6, 130.1, 128.6, 128.2, 127.7, 127.2, 126.6, 126.2, 114.1, 55.3.…”

Phosphazene-Catalyzed Regioselective Condensation of Allyl Thioethers with Aldehydes: A Rapid Approach to 1,3-Dienyl Sulfides, -Sulfoxides and -Sulfones

“…5, 163.4, 153.4, 143.2, 142.4, 141.1, 140.4, 139.6, 139.5, 133.2, 132.4, 131.3, 131.0, 129.7, 129.4, 126.7, 123.2, 120.9, 114.5, 104.9, 104.5, 61.0, 60.9, 56.2, 56.1, 55.6 ppm. MS: m/z (%) = 204 (23), 188 (100), 173 (56), 158 (23), 145 (60), 117 (16), 115 (16) 4, 144.4, 143.6, 143.4, 143.3, 142.8, 142.4, 139.9, 139.8, 135.4, 133.4, 133.3, 131.0, 130.8, 130.6, 128.0, 127.5, 127.2, 125.5, 125.2, 125.0, 122.8, 120.5, 105.0, 104.6, 61.0, 60.9, 56.2, 56 1,2,3-trimethoxy-5-(4-phenylbuta-1,3-dien-1-yl)benzene (8) 23 Under an argon atmosphere, a mixture of 7a (90 mg, 0.25 mmol) and PdCl2(PPh3)2 (17.5 mg, 0.025 mmol) was dissolved with dry THF (4 mL).…”

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

“…10 Thus, the development of practical and efficient methods for their preparation is of great significance. 11,12 In 1995, Zhang and co-workers reported the first vinylation of benzylammonium salts with terminal alkenes catalyzed by palladium (Scheme 1a). 13 By means of the cross-electrophile reaction strategy, a Ni-catalyzed reductive coupling of organoammonium salts with vinyl acetates for the preparation of a series of olefins was developed by Shu and co-workers recently (Scheme 1b).…”