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. 2017 Dec 1;19(23):6280-6283.
doi: 10.1021/acs.orglett.7b02906. Epub 2017 Nov 11.

Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group

Xiao-Yang Chen  1 , Seyma Ozturk  1 , Erik J Sorensen  1
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Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group

Xiao-Yang Chen et al. Org Lett. .

Abstract

The direct Pd-catalyzed ortho C-H hydroxylation of benzaldehydes was achieved using 4-chloroanthranilic acid as the transient directing group, 1-fluoro-2,4,6-trimethylpyridnium triflate as the bystanding oxidant, and p-toluenesulfonic acid as the putative oxygen nucleophile. The unusual C-H chlorination and polyfluoroalkoxylation reactions signaled the importance of external nucleophiles to the outcome of Pd(IV) reductive eliminations.

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