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Dynamic Kinetic C(sp2)–Si Cross-Coupling with Si–B Reagents for the Atroposelective Construction of Unsymmetrical Heterobiaryls

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A dynamic kinetic C(sp 2 )–Si cross-coupling of heterobiaryl triflates and silylboronic acid esters as silicon pronucleophiles is reported. The deracemization reaction proceeds typically in high yields and with 99% ee when using Pd(acac) 2 as the precatalyst and CuCl as a cocatalyst, and ( R )-TolBINAP as the chiral ligand. The copper salt assists the transmetalation of the Si–B reagent, thereby accelerating the reaction and also improving enantioselectivity. The method tolerates a wide range of functional groups and heterocycles, and different silyl groups can be introduced.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c03243

Authors: Yao Xiao, Annika L. Bartelt, Elisabeth Irran, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: China Scholarship Council, Einstein Stiftung Berlin