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

  • J Org Chem. 2021 Mar 19;86(6):4877-4882. doi: 10.1021/acs.joc.1c00193.
Keith R Fandrick  1 ,  Nitinchandra D Patel  1 ,  Suttipol Radomkit  1 ,  Arindom Chatterjee  1 ,  Stefan Braith  2 ,  Daniel R Fandrick  1 ,  Carl A Busacca  1 ,  Chris H Senanayake  1
Affiliations
  • 1. Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
  • 2. Department of Chemical Development, Boehringer-Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach/Riß, Germany.
PMID: 33686865 DOI: 10.1021/acs.joc.1c00193
Abstract

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

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