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Copper(I)/N-Heterocyclic Carbene (NHC)-Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors.

flow synthesis

Jun 272016

Thumbnail image of graphical abstract

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.

Advanced Synthesis & Catalysis

Volume 355, Issue 18, pages 3517–3521, December 16, 2013

Adv. Synth. Catal. 2013, 355, 3517−3521.

Copper(I)/N-Heterocyclic Carbene (NHC)-Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors

Camille A. Correia¹,
D. Tyler McQuade^1,3,* and
Peter H. Seeberger^1,2

DOI: 10.1002/adsc.201300802, http://onlinelibrary.wiley.com/doi/10.1002/adsc.201300802/abstract

Correia, C. A., McQuade, D. T. and Seeberger, P. H. (2013), Copper(I)/N-Heterocyclic Carbene (NHC)-Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors. Adv. Synth. Catal., 355: 3517–3521. doi: 10.1002/adsc.201300802

Author Information

1Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
2Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany
3Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, USA

Email: D. Tyler McQuade (tyler.mcquade@mpikg.mpg.de; mcquade@chem.fsu.edu)

^*Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany