Addition of Benzyl Halides to Aldehydes and Imines Using Photoactivated TDAE: Access to 3,4-Dihydroisocoumarins, 1,2-Diarylethanols, and 1,2-Diarylcarbamates under Metal-Free Conditions

Cédric Spitz; Morgane Bertrand; Vincent Remusat; Thierry Terme; Patrice Vanelle

doi:10.1021/acs.joc.2c00074

Addition of Benzyl Halides to Aldehydes and Imines Using Photoactivated TDAE: Access to 3,4-Dihydroisocoumarins, 1,2-Diarylethanols, and 1,2-Diarylcarbamates under Metal-Free Conditions

J Org Chem. 2022 Mar 18;87(6):4483-4488. doi: 10.1021/acs.joc.2c00074. Epub 2022 Mar 8.

Authors

Cédric Spitz¹, Morgane Bertrand¹, Vincent Remusat¹, 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: 35258309
DOI: 10.1021/acs.joc.2c00074

Abstract

We describe herein the intermolecular addition reaction of benzyl halides to aldehydes and imines using photoactivated tetrakis(dimethylamino)ethylene (TDAE) as superphotoreductant. 3,4-Dihydroisocoumarins, 1,2-diarylethanols, and 1,2-diarylcarbamates were obtained with good functional group tolerance using simple, mild, and metal-free conditions.