Synthesis of Tri‐ and Tetrasubstituted Olefins by Palladium Cross‐Coupling Reaction.

Abstract

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trans-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications

“…Prepared following the general procedure using NaOH as the base in 78% yield (14.3 mg, 38.5 μmol) from ( Z )-1,2-diphenylbut-1-en-1-yl 4-methylbenzenesulfonate ( Z )-1y (18.6 mg, 49.0 μmol) and (4-(2-(dimethylamino)­ethoxy)­phenyl)­boronic acid 3 . It was obtained as a white solid; TLC R f 0.28 (CH 2 Cl 2 /EtOH 5%); 1 H NMR (CDCl 3 , 500 MHz) δ 7.39–7.30 (m, 2H), 7.32–7.19 (m, 2H), 7.20–7.05 (m, 6H), 6.76 (d, J = 9.1, 8.6 Hz, 2H), 6.55 (d, 2H), 3.95 (t, J = 5.7 Hz, 2H), 2.68 (t, J = 5.2 Hz, 2H), 2.45 (q, J = 7.4 Hz, 2H), 2.32 (s, 6H), 0.92 (t, J = 7.3 Hz, 3H); 13 C NMR (CDCl 3 , 126 MHz) δ 156.8, 143.9, 142.5, 141.5, 138.3, 135.7, 132.0 (2C), 129.8 (2C), 129.6 (2C), 128.2 (2C), 128.0 (2C), 126.6, 126.1, 113.5 (2C), 65.5, 58.3, 45.9, 29.2 (2C), 13.8; HR-MS 372.2297 (C 26 H 29 ON+H + ) calcd 372.2322.…”

“…All aryl sulfonates 1 used were known compounds and were prepared from the commercially available phenol derivatives according to the reported procedure . ( E )-1-Bromocyclooct-1-ene 1w and bromotriphenylethylene 1x were synthesized following a procedure described in the literature . Boronic acid 3 was prepared in two steps from 4-iodophenol using a reported procedure …”

Paintable Hybrids with Thermally Stable Dual Emission Composed of Tetraphenylethene-Integrated POSS and MEH-PPV for Heat-Resistant White-Light Luminophores

“…Tetrahydrofuran (FUJIFILM Wako Pure Chemical Industries, Ltd.) and triethylamine (Et 3 N) (Kanto Chemical Co., Inc.) were purified by passage through solvent purification columns under N 2 pressure. Octakis(3-aminopropyl) POSS hydrochloride (Amino-POSS), 72 4-(1,2,2-triphenylethenyl)benzaldehyde (1), 73 TPE, 74 and 1,4-bis(chloromethyl)-2-(2′-ethylhexyloxy)-5-methoxybenzene 75 were synthesized according to literature.…”

Reações De Acoplamento C-C E C-N Na Síntese De Chalconas Poliariladas: Obtenção De Compostos Potencialmente Bioativos E Estudo Fotofísico De Moléculas Fluorescentes

“…A síntese controlada de olefinas tetrassubstituídas é um importante desafio em síntese orgânica (FLYNN; OGILVIE, 2007; NUNES; STEFFENS; MONTEIRO, 2007;ZHOU;EMRICH;LAROCK, 2003). Além disso, poliarilolefinas possuem importantes aplicações farmacológicas (JORDAN, 2003a(JORDAN, , 2003bSHARMA et al, 2010) e servem como substratos desafiadores para novos catalisadores de hidrogenação (JOHNSON et al, 2007;SCHREMS;NEUMANN;PFALTZ, 2007).…”