Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes

Mélodie Birepinte, Pier Alexandre Champagne, Jean François Paquin

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Abstract

A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF5Cl and (TMS)3SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ6-sulfanes (Z:E : >85:15), thus allowing the preparation of this previously unknown geometrical isomer. DFT calculations highlight that the selectivity is due to the intrinsic preference of SF5-substituted vinylic radicals to adopt a cis geometry, and to increased steric contacts during the transition structures leading to the minor (E)-products.

Original languageEnglish (US)
Article numbere202112575
JournalAngewandte Chemie - International Edition
Volume61
Issue number1
DOIs
StatePublished - Jan 3 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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