1319746-10-5Relevant articles and documents
Insertion of benzyne into a Bi-S bond: A new synthetic route to ortho -functionalized bismuthanes and its application to the synthesis of dibenzothiophene
Chen, Jing,Murafuji, Toshihiro,Tsunashima, Ryo
, p. 4532 - 4538 (2011/11/13)
ortho-Arylthio triarylbismuthanes [2-(Ar′S)C6H 4]nBiAr3-n have been conveniently synthesized by insertion of benzyne into the bismuth-sulfur bond of (Ar′S) nBiAr3-n (n = 1, 2). A similar insertion takes place when a homologous antimony congener is used, but no reaction is observed with its phosphorus analogue. This suggests a clear difference in the bond strength between pnictogen-sulfur bonds. The carbon-bismuth bond of [2-(2-BrC 6H4S)C6H4]nBiAr 3-n undergoes Pd-catalyzed intramolecular cross-coupling to produce dibenzothiophene in good yield. An X-ray crystallographic study of 2-(2-BrC 6H4S)C6H4BiTol2 (Tol = 4-MeC6H4) reveals that this molecule is present in a dimeric structure, where the six heteroatoms including bismuth, sulfur, and bromine are linked through the nonbonded intramolecular bismuth-sulfur and intermolecular sulfur-bromine and bromine-bromine interactions.