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29 Sep 09:04

[ASAP] Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

by J. Luca Schwarz, Felix Schäfers, Adrian Tlahuext-Aca, Lukas Lückemeier, Frank Glorius

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.8b08052
03 Dec 14:08

Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated CH Functionalization and the Minisci Reaction

by Jian Jin, David W. C. MacMillan

Abstract

The direct α-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated C[BOND]H functionalization pathway. Transiently generated α-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst.

Thumbnail image of graphical abstract

Use visible light! The direct α-arylation of cyclic and acyclic ethers with heteroarenes can be achieved at room temperature through a photoredox-mediated C[BOND]H functionalization pathway. This mild, visible-light-driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst. SET=single-electron transfer.