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Issue 13, 2019
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PdII-Catalyzed methoxylation of C(sp3)–H bonds adjacent to benzoxazoles and benzothiazoles

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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.

Graphical abstract: PdII-Catalyzed methoxylation of C(sp3)–H bonds adjacent to benzoxazoles and benzothiazoles

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Article information


Submitted
11 Feb 2019
Accepted
05 Mar 2019
First published
06 Mar 2019

Org. Biomol. Chem., 2019,17, 3314-3318
Article type
Communication

PdII-Catalyzed methoxylation of C(sp3)–H bonds adjacent to benzoxazoles and benzothiazoles

J. Kumar, A. Gupta and S. Bhadra, Org. Biomol. Chem., 2019, 17, 3314
DOI: 10.1039/C9OB00337A

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