Organic Chemistry Portal

Abstracts

Search:

A Noncoordinating Acid-Base Catalyst for the Mild and Nonreversible tert-Butylation of Alcohols and Phenols

Keith R. Fandrick*, Nitinchandra D. Patel, Suttipol Radomkit*, Arindom Chatterjee, Stefan Braith, Daniel R. Fandrick, Carl A. Busacca and Chris H. Senanayake

*Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email: keithfandgmail.com, suttipol.radomkitboehringer-ingelheim.com

K. R. Fandrick, N. D. Patel, S. Radomkit, A. Chatterjee, S. Braith, D. R. Fandrick, C. A. Busacca, C. H. Senanayake, J. Org. Chem., 2021, 86, 4877-4882.

DOI: 10.1021/acs.joc.1c00193


Abstract

A noncoordinating acid-base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] mediates a mild and nonreversible tert-butylation of alcohols and phenols with tert-butyl 2,2,2-trichloroacetimidate as a tert-butylation reagent. This method allows the use of substrates containing acid sensitive groups such as ketal, Boc, and boronate esters.

see article for more examples



Key Words

tert-butyl ethers


ID: J42-Y2021