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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: A dynamic kinetic C(sp2)–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: DepositOnce

DOI: 10.14279/depositonce-24669

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

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W7125812352

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