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Intermolecular and Intramolecular, Platinum-Catalyzed, Acceptorless Dehydrogenative Coupling of Hydrosilanes With Aryl and Aliphatic Methyl C-H Bonds

Intermolecular and Intramolecular, Platinum-Catalyzed, Acceptorless Dehydrogenative Coupling of Hydrosilanes With Aryl and Aliphatic Methyl C-H Bonds

Naofumi Tsukada, John F Hartwig

J Am Chem Soc. 2005 Apr 13;127(14):5022-3.

PMID: 15810828

Abstract:

Intermolecular acceptorless dehydrogenative coupling of silanes with arene C-H bonds and intramolecular coupling of silanes with aryl and alkyl C-H bonds occur in good yield in the presence of 5 mol % of TpMe2PtMe2H (TpMe2 = hydridotris(3,5-dimethylpyrazolyl)borate) and related platinum(IV) complexes. The intermolecular reactions of arenes occurred with both trialkyl and dialkylaryl silanes. Intramolecular reactions of dialkylsilylalkylarenes occurred at aryl C-H bonds, and reactions of tributylsilane or dibutylphenylsilane occurred intramolecularly at the aliphatic, primary C-H bond. The reactions of arenes occurred preferentially at the least sterically hindered C-H bonds and preferentially with more electron-poor arenes. Crossover experiments and the lack of reactivity of the arylsilanes with H2 imply that the dehydrogenative silylation of arenes can be irreversible, even in a closed reaction vessel.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18765098	Trioctylsilane		18765-09-8	Price

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