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: keithfand
gmail.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.
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Key Words
ID: J42-Y2021
