Facile Palladium-Catalyzed Carbonylation of Triarylstibines in the Presence of Ammonium Cerium(IV) Nitrate

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

“…Organoantimony chemistry has witnessed a considerable increase in interest due to its applications in coordination chemistry, organic synthesis, and biological medicine. − The traditional methods for the synthesis of stibine reagents involve the stoichiometric reactions of organolithium reagents or Grignard reagents with halostibines (Scheme a), as well as the reaction of organic halides with R 2 Sb–M (M = Li, Na, and K) (Scheme b). − The first catalytic process for C–Sb bond formation was achieved via the Pd-catalyzed Stille cross-coupling of in situ- prepared and air-sensitive Bu 3 SnSbPh 2 with ArI (Scheme c). , Very recently, our group reported the Ni-catalyzed Suzuki cross-coupling of halostibines with aryl/alkyl boronic acids (Scheme d) . Some pioneering works with isolated stibines for Pd-catalyzed transformation have also been published (Scheme d–i).…”

Microwave-Assisted Debromination of α-Bromoketones with Triarylstibanes in Water

“…[1][2][3] In particular, trivalent organoantimony(III) compounds (stibanes) have been used for a wide variety of transformations such as alkylation of carbonyl compounds, 4) Pd-catalyzed cross-coupling reactions, [5][6][7][8][9][10][11] photochemical reaction, 12) catalytic oxidative cyclization, 13) and asymmetric reactions with optically active compounds. [14][15][16][17][18] Stibane reagents such as triphenylstibane have low toxicity, [19][20][21] and are therefore promising reagents in organic synthesis.…”

“…The optimum amounts of the triarylstibane reagent, and active substrates, and microwave irradiation condition for this reaction are shown in entries 5-17. When water was used as the solvent, superior results were obtained in comparison with the solvent mixture of dioxane-H 2 O by conventional heating (entries 4,6). This reaction may be considered as a stoichiometric reaction between 1a and 3a because decreasing the amount of 3a reduces the yield of 4a (entries 6-8).…”

Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

“…[1][2][3][4][5] As for the application of trivalent organoantimony compounds (stibanes), a wide variety of reactions such as self-coupling reactions, 6,7) cross-coupling reactions, [8][9][10][11][12][13] photoreaction, 14) and asymmetric reactions with optically active organoantimony compounds [15][16][17][18][19] have been reported during the last two decades. On the other hand, the conversion of benzoin into benzil has been accomplished by oxidation with a variety of reagents; i.e., bismuthane oxide, 20) bismuthane imides, 21) alumina-supported copper sulfate under microwave irradiation, 22) and the Burgess reagent, 23) and by transition metal-catalyzed oxidation with bismuth nitrate-copper acetate, 24) aerobic oxygen, 25,26) diacetoxyiodobenzene, 27) and allyl diethyl phosphate.…”