Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

07 January 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal ortho-, distal meta- and para-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(sp2)-H functionalization via reversible imine formation. By overruling facile proximal C-H bond activation by imine-N atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.

Keywords

transient directing groups
imine

Supplementary materials

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