Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols

Cédric Spitz; Mélanie Matteudi; Guillaume Tintori; Julie Broggi; Thierry Terme; Patrice Vanelle

doi:10.1021/acs.joc.0c02374

Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols

J Org Chem. 2020 Dec 4;85(23):15736-15742. doi: 10.1021/acs.joc.0c02374. Epub 2020 Nov 23.

Authors

Cédric Spitz¹, Mélanie Matteudi¹, Guillaume Tintori¹, Julie Broggi¹, Thierry Terme¹, Patrice Vanelle¹

Affiliation

¹ Aix Marseille Univ, CNRS, ICR UMR CNRS 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, Cedex 05 13385 Marseille, France.

PMID: 33226220
DOI: 10.1021/acs.joc.0c02374

Abstract

We report here the intermolecular metal-free addition reaction of functionalized benzyl halides to aldehydes using a super electron donor (SED). The metal-free and mild conditions allowed the formation of 3,4-dihydroisocoumarins and 1,2-diarylethanols with unprecedented functional group tolerance.