A Structurally Characterized Fluoroalkyne

Lewis Marshall Hall, David Tew, Natalie Estelle Pridmore, Adrian C. Whitwood, Jason Martin Lynam, John Martin Slattery

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The facile synthesis of a stable and isolable compound with a fluoroalkynyl group, M−C≡CF, is reported. Reaction of [Ru(C≡CH)(η 5-C 5Me 5)(dppe)] with an electrophilic fluorinating agent (NFSI) results in the formation of the fluorovinylidene complex [Ru(=C=CHF)(η 5-C 5Me 5)(dppe)][N(SO 2Ph) 2]. Subsequent deprotonation with LiN(SiMe 3) 2 affords the fluoroalkynyl complex [Ru(C≡CF)(η 5-C 5Me 5)(dppe)]. In marked contrast to the rare and highly reactive examples of fluoroalkynes that have been reported previously, this compound can be readily isolated and structurally characterized. This has allowed the structure and bonding in the CCF motif to be explored. Further electrophilic fluorination of this species yields the difluorovinylidene complex [Ru(C=CF 2)(η 5-C 5Me 5)(dppe)][N(SO 2Ph) 2].

Original languageEnglish
Pages (from-to)7551-7556
Number of pages7
JournalAngewandte Chemie International Edition
Issue number26
Early online date23 May 2017
Publication statusPublished - 19 Jun 2017

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© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details


  • alkynes
  • alkynyls
  • electrophilic fluorination
  • fluorine
  • vinylidenes

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