TY - JOUR
T1 - Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes
AU - Birepinte, Mélodie
AU - Champagne, Pier Alexandre
AU - Paquin, Jean François
N1 - Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/1/3
Y1 - 2022/1/3
N2 - 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.
AB - 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.
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U2 - 10.1002/anie.202112575
DO - 10.1002/anie.202112575
M3 - Article
C2 - 34716642
AN - SCOPUS:85119887291
SN - 1433-7851
VL - 61
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 1
M1 - e202112575
ER -