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

XiaoYang Chen | Zendy; Seyma Ozturk | Zendy; Erik J. Sorensen | Zendy

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

Author(s) -

XiaoYang Chen,

Seyma Ozturk,

Erik J. Sorensen

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02906

Subject(s) - chemistry , hydroxylation , nucleophile , catalysis , trifluoromethanesulfonate , medicinal chemistry , group (periodic table) , oxygen , organic chemistry , enzyme

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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