Pd-Catalyzed methoxylation of C(sp)-H bonds adjacent to benzoxazoles and benzothiazoles.

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2019
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Abstract
The Pd(OAc)2/PhI(OAc)2 catalyst system promotes the highly regioselective dehydrogenative methoxylation of a C(sp3)-H bond adjacent to benzoxazole and benzothiazole rings. The title transformation constitutes the first example of a Pd-catalyzed C(sp3)-H activating methoxylation at the proximal-selective α-position with regard to a directing auxiliary and provides expedient access to an important class of azole-decorated methyl ethers (up to 90% isolated yield). The synthetic practicality of the methodology was demonstrated by achieving α-methoxyacetic acids via the elimination of the benzoxazole auxiliaries and by obtaining the precursor of an O-methylated Breslow intermediate.
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kumar2019pdcatalyzedorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Kumar, Jogendra;Gupta, Aniket;Bhadra, Sukalyan;
Journal Organic & biomolecular chemistry
Year 2019
DOI
10.1039/c9ob00337a
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Keywords
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