20265-30-9Relevant articles and documents
Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes
Arias Ugarte, Renzo,Devarajan, Deepa,Mushinski, Ryan M.,Hudnall, Todd W.
supporting information, p. 11150 - 11161 (2016/07/20)
1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.
Triorganoantimony(V) carboxylates: Synthesis, characterization and crystal structure of [Me3Sb(O2C-C5H4N)2] · H2O
Chaudhari, Kamal R.,Jain, Vimal K.,Sagoria,Tiekink, Edward R.T.
, p. 4928 - 4932 (2008/03/13)
Reactions of [R3Sb(OPri)2] with N-heterocylic carboxylic acids gave compounds of the type [R3Sb(O2C-Ar)2] (1) (R = Me, Et, Pri, Ph; Ar = 2-C5H4N, 2-C9
Pd-catalyzed C-arylation of unsaturated compounds with pentavalent triarylantimony dicarboxylates
Moiseev, Dmitry V.,Gushchin, Aleksey V.,Shavirin, Andrey S.,Kursky, Yury A.,Dodonov, Viktor A.
, p. 176 - 184 (2007/10/03)
Triarylantimony (V) derivatives Ar3SbX2 (X = Hal or acyloxy) were prepared by reaction of Ar3Sb with equimolar amounts of a peroxide ROOH (R = t-Bu, H) in the presence of an acid or an anhydride in good to excellent yields. Ar3Sb(O2CR)2 are mild and efficient C-arylation reagents of unsaturated compounds (methyl acrylate, styrene, 2-phenylpropene and acrylonitrile) under palladium catalysis at 50 °C, with PdCl2 being the most effective catalyst. Ar3SbHal2 do not react under these conditions.
