Mild and Metal-Free Protocol toward the Synthesis of Triarylmethanes by Reactions of (Hetero)Arylboronic Acids and ortho-Hydroxyarylaldehydes

Irfana Jesin C P; A Antony Haritha Mercy; Ravindra S; Ramesh Kataria; Ganesh Chandra Nandi

doi:10.1021/acs.joc.9b02807

Mild and Metal-Free Protocol toward the Synthesis of Triarylmethanes by Reactions of (Hetero)Arylboronic Acids and ortho-Hydroxyarylaldehydes

J Org Chem. 2020 Mar 6;85(5):3000-3009. doi: 10.1021/acs.joc.9b02807. Epub 2020 Feb 10.

Authors

Irfana Jesin C P¹, A Antony Haritha Mercy¹, Ravindra S¹, Ramesh Kataria², Ganesh Chandra Nandi¹

Affiliations

¹ Department of Chemistry, National Institute of Technology, Tiruchirappalli 620015, Tamilnadu, India.
² Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India.

PMID: 31927895
DOI: 10.1021/acs.joc.9b02807

Abstract

Herein, we have reported a metal-free, mild, and novel protocol for the synthesis of various triarylmethanes (TRAMs) in moderate to good yields via the reactions of aryl boronic acids and ortho-hydroxyarylaldehydes in the presence of stoichiometric amounts of Et₃N in dichloroethane at 80 °C. Additionally, the synthetic utilities of few synthesized TRAMs were proven by carrying out bromination on the -OH-containing aryl part and followed by functionalization of bromine through a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with arylboronic acids in good yields. The -OH group was also alkylated and arylated through simple alkylation and Chan-Lam reaction, respectively.