Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines

Ultrafast charge transfer of stiboviologens for electrochromism and visible light-induced α-amino C(sp3)–H functionalization

“…[37][38][39][40][41] Organic antimony compounds oen exist in the trivalent or pentavalent form due to the electron conguration of Sb. These compounds, characterized by their heavier atoms, distinctive electron conguration, and certain biocompatibility, 42,43 have been widely applied in organic synthesis, [44][45][46] photocatalysis, [47][48][49] and coordination chemistry. [50][51][52] However, many organic antimony systems, primarily coordination systems, suffer from instability when exposed to air and water.…”

Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

“…Moreover, a number of research groups have reported the use of trivalent stibines as coupling partners in Heck-type reactions (Scheme f). − In 2018, Simpson et al described the oxidative cross-coupling of aryl-boron nucleophiles with triarylantimony (Scheme g) . In addition, Kurita and Kakusawa reported the use of 6-( tert -butyl)-12-aryl-5,6,7,8-tetrahydrodibenz­[ c , f ]­[1,5]­aza stibocines as transmetallating agents for the arylation of aryl iodides, but its potential as a powerful and robust nucleophile reagent for reaction with organic halides was unclear (Scheme h) (see the Supporting Information, Tables S12 and S13) .…”

Pd-Catalyzed Cross-Coupling of Sb-Aryl Stibines with Halogenomethyl Arenes to Give Unsymmetirc Diarylmethanes

“…The Pd-catalyzed alkynylation of aryl iodides and vinyl and acyl halides with Sb -alkynl stibines was disclosed by Kurita (Scheme a) . Subsequently, the use of trivalent stibines in Heck-type reactions and the arylation of arenes , was also revealed (Scheme b). Our group developed the palladium-catalyzed oxidative cross-coupling reaction of organostibines for the site-selective synthesis of biaryls , and unsymmetric (1 E ,3 E )-1,4-diarylbuta-1,3-dienes; halostbines could be also recycled from the reaction system (Scheme a) …”