Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group.

ABSTRACT: Transient directing groups (TDGs) can provide a powerful means for C-H functionalization without requiring additional steps for directing group introduction and removal. We report the first use of a TDG in combination with copper to effect C-H functionalization. The regioselective copper mediated β-C(sp² )-H sulfonylation of aldehydes with sulfinate salts is accomplished using catalytic β-alanine to form a transient imine. A broad range of sulfonylated benzaldehydes are prepared using copper fluoride as both copper source and oxidant, involving a [5,6] cupracyclic intermediate. γ-(peri)-Sulfonylation of napthyl and phenanthrenyl carboxaldehydes is achieved through [6,6] cupracyclic intermediates. Further derivatisation of the aldehyde products is demonstrated. Kinetic experiment

SUBMITTER: Higham JI 

PROVIDER: S-EPMC9321081 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature