Premium
Aryl Radical‐Mediated Alkenylation of Alkyl Halides
Author(s) -
Chaambi Ahmed,
Kurtay Gülbin,
Abderrahim Raoudha,
Robert Frédéric,
Landais Yannick
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900140
Subject(s) - triethylamine , aryl , alkyl , chemistry , iodide , halide , photochemistry , electron acceptor , electron transfer , iodine , medicinal chemistry , aryl radical , acceptor , organic chemistry , physics , condensed matter physics
The free‐radical alkenylation of a range of alkyl iodides with a vinyldisulfones has been carried out, leading to the desired vinylsulfones in moderate to good yields under mild conditions. The process is initiated by an aryl radical which abstracts the iodine atom from the alkyl iodide to form a C‐centered radical intermediate, the addition of which onto the vinyldisulfone providing the final vinylsulfone. The aryl radical is generated in situ through a single‐electron transfer from an electron donor‐acceptor complex (EDA) formed between a diaryliodonium salt (Ph 2 I + PF 6 − ) and triethylamine.