Work

Enantio‐ and Regioconvergent Nickel‐Catalyzed Etherification of Phenols by Allylation to Access Chiral C(sp3)−O Allyl Aryl Ethers

Year: 2024

Type: article

Abstract: An enantio- and regioconvergent allylation of phenols under nickel catalysis with an α-/γ-regioisomeric mixture of racemic silylated/germylated allylic chlorides is reported. The silyl/germyl group governs the regioselectivity, and the transformation affords enantiomerically enriched unsymmetrical 1,3-disubstituted allyl aryl ethers with excellent regiocontrol in good yields and excellent enantioselectivities. Notably, no nickel-mediated C-O bond activation is observed at room temperature. The synthetic value of these densely functionalized silicon-containing building blocks is demonstrated in a series of chemoselective transformations, including a [3,3]-sigmatropic rearrangement for the construction of an α-chiral silane.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202412181

Authors: Daniel Brösamlen, Daniel Neb, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Deutsche Forschungsgemeinschaft, Einstein Stiftung Berlin