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

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0015-3784-A Version Permalink: http://hdl.handle.net/21.11116/0000-0006-6005-8
Genre: Journal Article

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1921763.pdf (Publisher version), 179KB
 
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 Creators:
Correia, Camille A.1, Author              
McQuade, D. Tyler2, Author              
Seeberger, Peter H.3, Author              
Affiliations:
1Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863304              
2Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863286              
3Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 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.

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 Dates: 2013
 Publication Status: Published in print
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 Identifiers: ISI: 000329021600002
DOI: 10.1002/adsc.201300802
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Title: Advanced Synthesis & Catalysis
  Abbreviation : Adv. Synth. Catal.
Source Genre: Journal
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Publ. Info: Weinheim, Fed. Rep. of Germany : Wiley-VCH Verlag GmbH
Pages: - Volume / Issue: 355 (18) Sequence Number: - Start / End Page: 3517 - 3521 Identifier: ISSN: 1615-4150