PdII-Catalyzed methoxylation of C(sp3)-H bonds adjacent to benzoxazoles and benzothiazoles
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.
Kumar, Jogendra,Gupta, Aniket,Bhadra, Sukalyan
p. 3314 - 3318
(2019/04/01)
Structures and reactivities of O-methylated Breslow intermediates
As close as you can get: Since Breslow intermediates usually exist in their keto form, their O-protected tautomers may be considered as their closest isolable relatives. A series of these compounds have been synthesized, their structures determined, and the kinetics of their reactions with electrophiles investigated. Copyright
Maji, Biplab,Mayr, Herbert
supporting information
p. 10408 - 10412
(2012/11/07)
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