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Copper(I)/N-heterocyclic carbene (NHC)-catalyzed addition of terminal alkynes to trifluoromethyl ketones for use in continuous reactors

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Correia,  Camille A.
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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McQuade,  D. Tyler
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Correia, C. A., McQuade, D. T., & Seeberger, P. H. (2013). Copper(I)/N-heterocyclic carbene (NHC)-catalyzed addition of terminal alkynes to trifluoromethyl ketones for use in continuous reactors. Advanced Synthesis & Catalysis, 355(18), 3517-3521. doi:10.1002/adsc.201300802.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0015-3784-A
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.