Co/Fe Dual Catalysis for Sequential Hydrosilylation–Isomerization: Access to Trisubstituted (E)-Alkenyl Silanes from Terminal Alkynes

Zhihao Guo , Guixia Liu , Zheng Huang

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (16) : 1860 -1866.

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Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (16) : 1860 -1866. DOI: 10.1002/cjoc.202400291
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Co/Fe Dual Catalysis for Sequential Hydrosilylation–Isomerization: Access to Trisubstituted (E)-Alkenyl Silanes from Terminal Alkynes

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Abstract

By rational modification of electronic and steric properties of pincer ligands, a Co/Fe dual catalyst system is developed for one-pot sequential Markovnikov alkyne hydrosilylation and stereoselective alkene isomerization. The protocol provides an atom-economical and efficient approach to trisubstituted ( E)-alkenyl silanes from widely accessible terminal alkynes with high regio- and stereoselectivities under mild conditions. The utility of this reaction was demonstrated by gram-scale synthesis and derivatization of bioactive molecules. The radical clock and trapping experiments indicated that radical pathway might be operative in the alkene isomerization step.

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Cobalt / Dual catalysis / Hydrosilylation / Iron / Isomerization / Trisubstituted alkenyl silanes

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Zhihao Guo, Guixia Liu, Zheng Huang. Co/Fe Dual Catalysis for Sequential Hydrosilylation–Isomerization: Access to Trisubstituted (E)-Alkenyl Silanes from Terminal Alkynes. Chinese Journal of Chemistry, 2024, 42(16): 1860-1866 DOI:10.1002/cjoc.202400291

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