Controlling Pd(IV) reductive elimination pathways enables Pd(II)-catalysed enantioselective C(sp³)-H fluorination.

ABSTRACT: The development of a Pd(II)-catalysed enantioselective fluorination of C(sp³)-H bonds would offer a new approach to making chiral organofluorines. However, such a strategy is particularly challenging because of the difficulty in differentiating prochiral C(sp³)-H bonds through Pd(II)-insertion, as well as the sluggish reductive elimination involving Pd-F bonds. Here, we report the development of a Pd(II)-catalysed enantioselective C(sp³)-H fluorination using a chiral transient directing group strategy. In this work, a bulky, amino amide transient directing group was developed to control the stereochemistry of the C-H insertion step and selectively promote the C(sp³)-F reductive elimination pathway from the Pd(IV)-F intermediate. Stereochemical an

SUBMITTER: Park H 

PROVIDER: S-EPMC6289870 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature