Use of triarylstibines in C -arylation reactions

Tetraphenylantimony carboxylates in the cascade Pd-catalyzed C-phenylation reaction of methyl acrylate in the presence of peroxide

“…Moreover, Ph 3 Sb can deactivate a palladium catalyst [3]. We assumed that an addition of organic peroxide in the reaction mixture in the presence of a carboxylic acid could convert Ph 3 Sb into triphenylantimony dicarboxylate in situ [4]. The latter is an active phenylating agent [3,4].…”

“…We assumed that an addition of organic peroxide in the reaction mixture in the presence of a carboxylic acid could convert Ph 3 Sb into triphenylantimony dicarboxylate in situ [4]. The latter is an active phenylating agent [3,4]. We investigated the model C-phenylation reaction of methyl acrylate 1 with tetraphenylantimony hydroxide Ph 4 SbOH 2 (1:2 ¼ 4:1) in AcOH in the presence of tBuOOH 3 (1.2 equivalent per 2) and Li 2 PdCl 4 (4 mol%).…”

“…It is one of the most accessible compounds of this type and can easy give tetraphenylantimony acetate Ph 4 SbOAc 4 in AcOH solution [6,7] (Scheme 1). Peroxide 3 is the best oxidant for antimony(III) derivatives [4]. Li 2 PdCl 4 is the optimum precatalyst for the C-phenylation in the presence of the peroxide [4].…”

“…We have recently reported that triarylantimony dicarboxylates were efficient reagents in the palladium-catalyzed C-arylation reactions of unsaturated compounds with the involvement of two aryl groups [3]. Triarylstibines Ar 3 Sb can also be used as reagents in the C-arylation reaction via formation of Ar 3 Sb(OAc) 2 in situ in the presence of peroxides [4]. Tetraphenylantimony derivatives Ph 4 SbX have shown lower activities in comparison with Ar 3 Sb(OAc) 2 .…”

Experimental study of electron density distribution in crystals of antimony(V) dicarboxylate complexes

“…Other triaryldicarboxylate complexes of Sb(V) exhibit antitumor [5][6][7][8][9] activity. Also these compounds are successfully used as catalysts in crosscoupling reaction [10][11][12][13][14]. In spite of visible interest to triarylantimony(V) carboxylate complexes, there are no data about their experimental charge density.…”