Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes

Organic Letters
Song LiTeck-Peng Loh

Abstract

An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp *Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation.

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Citations

Sep 19, 2019·Chemistry, an Asian Journal·Tariq A ShahTharmalingam Punniyamurthy

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