Synthesis of carbinoxamine via α-C(sp³)-H 2-pyridylation of O, S or N-containing compounds enabled by non-D-A-type super organoreductants and sulfoxide- or sulfide HAT reagents.

ABSTRACT: The radical cations of tertiary amines (R₃N) have been well-established as the precursors of HAT reagents in photochemical transformations. Similarly, thiols and thioacids bearing SH groups have also been widely applied as HAT reagents. Despite the fact that sulfoxides (R₂SO) and sulfides (RSR) also bear lone pairs of electrons, these compounds have been barely reported as HAT reagents in photocatalysis. On the other hand, the α-C-H 4-pyridylation of O or N-containing compounds has been documented, whereas 2-pyridylation remains challenging. However, the antihistamine and anticholinergic agent carbinoxamine is an ether bearing 2-pyridyl, which has not been obtained by the existing α-photoarylation of ether. In this work, we report the discovery of a non-donor-acceptor

SUBMITTER: Cui XC 

PROVIDER: S-EPMC9517729 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature