Ir-Catalyzed Synthesis of Substituted Tribenzosilepins by Dehydrogenative C-H/Si-H Coupling.

J Org Chem

Global Center for Science and Engineering, School of Advanced Science and Engineering , Waseda University, 3-4-1 Okubo , Shinjuku, Tokyo 169-8555 , Japan.

Published: April 2018

The Ir-catalyzed intramolecular reaction of 2',6'-diaryl-2-(hydrosilyl)biphenyls gave substituted tribenzosilepins by direct dehydrogenative C-H/Si-H coupling. This is the first example of catalytic construction of the tribenzosilepin skeleton. Enantiomerically pure tribenzosilepin was prepared by optical resolution using chiral HPLC, and its inversion barrier was calculated by measurement of rate of racemization using the Eyring kinetic equation under heating conditions.

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http://dx.doi.org/10.1021/acs.joc.8b00233DOI Listing

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