Deoxygenative Borylation of Secondary and Tertiary Alcohols
Authors:
Open Access
- 3 May 2019
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 58 (28) , 9561-9564
Abstract
Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal‐free silyl‐radical‐mediated pathway or utilize visible‐light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional‐group tolerance, and are conducted under mild and practical conditions.Keywords
Funding Information
- H2020 European Research Council (ERC Advanced Grant agreement No. 692640)
This publication has 47 references indexed in Scilit:
- Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction PartnersChemical Reviews, 2011
- Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling ReactionsAngewandte Chemie International Edition, 2009
- Sekundäre Alkylhalogenide in übergangsmetallkatalysierten KreuzkupplungenAngewandte Chemie, 2009
- Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted AllenylboronatesJournal of the American Chemical Society, 2008
- Catalysts for Cross‐Coupling Reactions with Non‐activated Alkyl HalidesAngewandte Chemie International Edition, 2005
- Katalysatoren machen's möglich: Selektive C‐C‐Kupplungen mit nichtaktivierten AlkylhalogenidenAngewandte Chemie, 2005
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Tris(trimethylsilyl)silane as a radical-based reducing agent in synthesisThe Journal of Organic Chemistry, 1991
- A new method for the radical deoxygenation of tertiary alcoholsJournal of the Chemical Society, Chemical Communications, 1984
- A new method for the deoxygenation of secondary alcoholsJournal of the Chemical Society, Perkin Transactions 1, 1975