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Copper(I)/N‐Heterocyclic Carbene (NHC)‐Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors
Author(s) -
Correia Camille A.,
McQuade D. Tyler,
Seeberger Peter H.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300802
Subject(s) - trifluoromethyl , chemistry , carbene , aryl , catalysis , ketone , copper , combinatorial chemistry , continuous flow , efavirenz , trifluoromethylation , substrate (aquarium) , organic chemistry , medicinal chemistry , alkyl , oceanography , medicine , family medicine , human immunodeficiency virus (hiv) , antiretroviral therapy , viral load , geology , physics , mechanics
A copper(I)/N‐heterocyclic carbene complex‐catalyzed addition of terminal alkynes to trifluoromethyl ketones at low loading is described. The developed process functions well using a range of terminal alkynes but functions best when an aryl trifluoromethyl ketone is used. This substrate scope is well‐suited for the production of active pharmaceutical ingredients (APIs) such as efavirenz. In this vein, we demonstrate that the described method can be translated into a flow process laying the framework for a completely continuous synthesis of efavirenz in the future.