Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 7-8, Pages 1080-1088Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900029
Keywords
boranes; 1,1-carboboration; Lewis acids; siloles
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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The strong Lewis acid tris(pentafluorophenyl)borane [B(C6F5)(3)] reacts rapidly with dimethylbis(phenylethynyl)silane (1c) at room temperature In toluene by shift of a pentafluorophenyl (C6F5) group and formation of a new carbon-bis(pentafluorophenyl)boron linkage [C-B(C6F5)(2)] in a sequence of 1,1-carboboration reactions to yield the 4-bis(pentafluorophenyl)boryl/3-pentafluorophenyl- substituted 1,1-dimethyl-2,5-diphenylsilole derivative 7c. The analogous reaction of bis(trimethylsilylethynyl)diphenylsilane (1d) with tris(pentafluorophenyl)borane gave the corresponding boryl-substituted silole derivative (7d) featuring six bulky substituents attached at the central heterocyclic frarnework. Both the starting materials (1c, 1d) and the products (7c, 7d) were characterized by X-ray crystal structure analyses.
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