The transition metal catalyzed directed C-H activation strategy is one of the most straightforward and site-selective approaches in organic chemistry for constructing C-C bonds. In particular, directed C-H alkylations with alkenes provides an atom economic protocol for forming the C-C bond. In 1993, Murai reported a ketone-directed strategy for the Ru-catalyzed <i>ortho</i>-C-H alkylation of aromatic ketones with alkenes. Following this pioneering reaction, numerous directing groups have been designed for use in regio-selective C-H alkylation reactions. It is noteworthy that most of the reports deal with linear-selective alkylation reactions. However, only a limited number of studies that deal with branch-selective C-H alkylation with alkenes have been reported. In this respect, all of these branch-selective alkylation reactions were achieved using styrenes, acrylate esters, vinyl ethers, and unactivated 1-alkenes. Nonetheless, branch-selective alkylation with vinylsilanes has not been achieved to date, although the linear selective alkylation with vinylsilanes with the aid of a directing group strategy have been widely explored. Given our long term interest in bidentate-chelation assisted Rh-catalyzed C-H alkylation reactions, herein we report an unusual Rh(II)-catalyzed branch-selective <i>ortho</i>-C-H alkylation of biologically important aryl sulfonamides with vinylsilanes by taking the advantage of an 8-aminoquinoline auxiliary. Moreover, deuterium labelling experiments provided insights into the reaction mechanism, in which involvement of two parallel catalytic pathways such as hydrometalation and carbometalation pathways are anticipated.

Rhodium(II)-catalyzed branch-selective C-H alkylation of benzenesulfonamide derivatives with vinylsilanes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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