Lewis Acid-Promoted Typical Friedel–Crafts Reactions Using DMSO as a Carbon Source

This study reports a mild and efficient synthetic protocol for the synthesis of symmetrical and unsymmetrical diarylmethanes (DAMs). Using DMSO as the C1 source and TMSOTf as the Lewis acid promoter, a series of functionalized symmetrical and unsymmetrical DAMs were synthesized in high yields. Grati...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2022-08, Vol.87 (15), p.10044-10053
Main Authors: Vodnala, Nagaraju, Singh, Sanjay, Hazra, Chinmoy Kumar
Format: Article
Language:English
Subjects:
anticoagulants
carbon
feedstocks
Lewis acids
moieties
organic chemistry
solvents
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This study reports a mild and efficient synthetic protocol for the synthesis of symmetrical and unsymmetrical diarylmethanes (DAMs). Using DMSO as the C1 source and TMSOTf as the Lewis acid promoter, a series of functionalized symmetrical and unsymmetrical DAMs were synthesized in high yields. Gratifyingly, DMSO plays a dual role as a solvent and a C1 source and can also be replaced with its deuterated counterpart, DMSO-d 6, enabling the incorporation of the -CD2 moiety into the diarylmethane skeleton. The developed approach has been applied to a wide range of substrates having various functional groups, and this protocol has also been extended to the synthesis of an anti-breast cancer agent and an anticoagulant agent using common feedstock compounds. In addition, the postulated mechanism has been explicitly demonstrated via control experiments.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.2c01037