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Atroposelective Pd-Catalyzed C( sp 2 )–P Coupling Enabling Modular Assembly of Axially Chiral QUINAPO Ligands

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide QUINAP ligands have been widely employed in a broad range of synthetically valuable asymmetric transformations, and their oxidized analogues, QUINAPOs, serve as effective Lewis base catalysts. Yet, a general and modular synthesis of these scaffolds has remained elusive. Herein, we present a Pd-catalyzed asymmetric C( sp 2 )–P coupling reaction of racemic heterobiaryl triflates with secondary phosphine oxides that furnishes axially chiral QUINAPOs in 47–98% yields and up to 95% ee across a broad substrate scope. The platform is diversity-oriented, enabling rapid access to structurally varied QUINAPO frameworks; subsequent deoxygenation delivers the corresponding QUINAP ligands. Representative members exhibit high activity and enantioselectivity in the asymmetric allylic alkylation and alkynylation of chromones, highlighting how ligand substitution modulates catalytic performance.

Source: JACS Au

DOI: 10.1021/jacsau.5c01633

Authors: Zhiping Yang, Jiangtao Cheng, Jun Wang

Institution: Hong Kong Baptist University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Hong Kong Baptist University, National Natural Science Foundation of China, University Grants Committee, K. C. Wong Education Foundation