Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes

Authors

Mélodie Birepinte, Université Laval
Pier Alexandre Champagne, New Jersey Institute of Technology
Jean François Paquin, Université Laval

Document Type

Article

Publication Date

1-3-2022

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.

Identifier

85119887291 (Scopus)

Publication Title

Angewandte Chemie International Edition

External Full Text Location

https://doi.org/10.1002/anie.202112575

e-ISSN

15213773

ISSN

14337851

PubMed ID

34716642

Issue

1

Volume

61

Fund Ref

Université Laval

Recommended Citation

Birepinte, Mélodie; Champagne, Pier Alexandre; and Paquin, Jean François, "Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes" (2022). Faculty Publications. 3184.
https://digitalcommons.njit.edu/fac_pubs/3184