Divalent Ytterbium Complex-Catalyzed Homo- and Cross-Coupling of Primary Arylsilanes - INSA Toulouse - Institut National des Sciences Appliquées de Toulouse Access content directly
Journal Articles Journal of the American Chemical Society Year : 2019

Divalent Ytterbium Complex-Catalyzed Homo- and Cross-Coupling of Primary Arylsilanes

Abstract

Redistribution of primary silanes through C-Si and Si-H bond cleavage and reformation provides a straightforward synthesis of secondary silanes, but the poor selectivity and low efficiency severely hinders the application of this synthetic protocol. Here, we show that a newly synthesized divalent ytterbium alkyl complex exhibits unprecedentedly high catalytic activity toward the selective redistribution of primary arylsilanes to secondary arylsilanes. More significantly, this complex also effectively catalyzes the cross-coupling between electron-withdrawing substituted primary arylsilanes and electron-donating substituted primary arylsilanes to secondary arylsilanes containing two different aryls. DFT calculation indicates that the reaction always involve the exothermic formation of a hypervalent silicon upon facile addition of PhSiH3 to the Yb-E (E = C, H) bond. This hypervalent compound can easily either generate directly the Yb-Ph complex, or indirectly through the formation of Yb-H, that is the key complex for the formation of Ph2SiH2.
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Dates and versions

hal-04022166 , version 1 (09-03-2023)

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Xiaojuan Liu, Li Xiang, Elisa Louyriac, Laurent Maron, Xuebing Leng, et al.. Divalent Ytterbium Complex-Catalyzed Homo- and Cross-Coupling of Primary Arylsilanes. Journal of the American Chemical Society, 2019, 141 (1), pp.138-142. ⟨10.1021/jacs.8b12138⟩. ⟨hal-04022166⟩
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