What question did this study set out to answer?

The aim is to achieve atroposelective synthesis of C-N axially chiral biaryls through distal C-H bond activation.

March 28, 2026

Atroposelective Synthesis of C–N Axially Chiral Biaryls via Catalytic C–H Functionalization at a Remote Site

Key Points

The aim is to achieve atroposelective synthesis of C-N axially chiral biaryls through distal C-H bond activation.
Utilized rhodium catalysis for C-H bond activation.
Investigated naphthalimides with bulky N-aryl groups.
Performed alkynylation or alkenylation via desymmetrization or parallel kinetic resolution.
Conducted mechanistic studies to assess enantiodetermining steps.
Achieved successful C-N axially chiral biaryl synthesis.
C-H bond activation was identified as enantiodetermining.
Demonstrated efficiency of carbonyl group-assisted C-H bond activation.

Abstract

Construction of axial chirality via distal functionalization consists of a significant challenge. Reported herein is the atroposelective synthesis of C-N axially chiral biaryls based on C-H bond activation at a site that is three bonds away from the axis atom. Under rhodium catalysis, naphthalimides bearing a bulky N-aryl group undergo carbonyl group-assisted C-H bond activation en route to alkynylation or alkenylation via desymmetrization or parallel kinetic resolution. Mechanistic studies indicate that C-H bond activation is likely enantiodetermining.

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Atroposelective Synthesis of C–N Axially Chiral Biaryls via Catalytic C–H Functionalization at a Remote Site

Key Points

Abstract

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