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Free‐Radical Carbo‐Alkenylation of Olefins: Scope, Limitations and Mechanistic Insights
Author(s) -
Beniazza Redouane,
Liautard Virginie,
Poittevin Clément,
Ovadia Benjamin,
Mohammed Shireen,
Robert Frédéric,
Landais Yannick
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605043
Subject(s) - alkene , sulfonyl , reactivity (psychology) , scope (computer science) , olefin fiber , chemistry , radical , acceptor , organic chemistry , photochemistry , catalysis , computer science , medicine , alkyl , alternative medicine , pathology , programming language , physics , condensed matter physics
The three‐component free‐radical carbo‐alkenylation of electron‐rich olefins has been studied, varying the substitution pattern in the alkene, in the radical precursor and in the final acceptor. New vinylsulfones were also prepared and their reactivity investigated. The scope and limitations of the process was established, and the reaction mechanism clarified using selected dienes as radical clocks. It was thus recognised that the reversible addition onto the olefin of the released sulfonyl group is an important event, which should not be overlooked when using such multicomponent carbo‐alkenylation reactions.