Palladium-Catalyzed Coupling Reaction of Vinyl Epoxides, Diol Acetonides, and Diol Carbonates With Organobismuth Compounds

Study of homo- and cross-coupling competition in the reaction of triarylbismuth(V) dicarboxylates with methyl acrylate in the presence of a palladium catalyst

“…Triarylbismuth has been used in the carbonylation reaction as well [13]. Arylation of vinyl epoxides, diol acetonides and diol carbonates has been performed with both triarylbismuth(III) and triarylbismuth(V) dichloride or carbonate [14]. Several types of organobismuth(III) compounds have been tested in Heck-type reactions [15][16][17].…”

Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols

“… 7 Owing to its unique structural features, vinyl epoxide is prone to S N 2′-type ring-opening/coupling reactions with aryl nucleophiles, affording alcohols containing a C C bond. Some research groups have reported ring-opening/coupling reactions of vinyl epoxide with various types of aryl nucleophiles, including aryl bismuth compounds, 8 aryl Grignard reagents, 9 aryl boron compounds, 10 aryl siloxane reagents, 11 and organotin compounds ( Scheme 1a ). However, these previously reported works all afford aryl-substituted allylic alcohols.…”

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides

“…Among them, triarylbismuth dichlorides (Ar 3 BiCl 2 ) have been widely used as aryl group donors for the C-and O-arylation of phenol derivatives [22][23][24], N-arylation of pyridin-2-ones [25,26], α-arylation of α,β-unsaturated carbonyls [27,28], and tandem 1,3-bisarylation of cyclopropanes with arenes [29]. They have also been used in Pd-catalyzed cross-coupling reactions to react with hypervalent iodonium salts, organostananes, and vinyl epoxides [30][31][32]. Moreover, there are reports of them serving as oxidizing agents for alcohols [33].…”