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Synfacts 2007(9): 0950-0950  
DOI: 10.1055/s-2007-968871
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Au-NHC-Catalyzed Hydrofluorination of Alkynes

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
J. A. Akana, K. X. Bhattacharyya, P. Müller, J. P. Sadighi*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

NHC-gold(I) fluoride complex 1 (prepared in situ) catalyzes the trans hydrofluorination of internal alkynes. For alkynes bearing both an alkyl and a phenyl substituent, β-fluoro­styrene products predominate. Further, electron-poor aryl substituents give higher regioselectivities than electron-rich ones. Addition of powdered KHSO4 as well as PhNMe2 ×HOTf greatly enhanced the yields, compensating for the decrease in acidity due to consumed HF.