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

Xiao Yang Chen; Seyma Ozturk; Erik J. Sorensen

doi:10.1021/acs.orglett.7b02906

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

Xiao Yang Chen, Seyma Ozturk, Erik J. Sorensen

Chemistry

Research output: Contribution to journal › Article › peer-review

82 Scopus citations

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.

Original language	English (US)
Pages (from-to)	6280-6283
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.7b02906
State	Published - Dec 1 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Chen, {Xiao Yang} and Seyma Ozturk and Sorensen, {Erik J.}",

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AU - Ozturk, Seyma

AU - Sorensen, Erik J.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - 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.

AB - 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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ER -

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

Abstract

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