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Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins
Author(s) -
Swain Manisha,
Sadykhov Gusein,
Wang Ruoxi,
Kwon Ohyun
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005267
Subject(s) - alkene , chemistry , alkylation , metathesis , styrene , combinatorial chemistry , natural product , double bond , organic chemistry , catalysis , polymerization , copolymer , polymer
The dealkenylative alkenylation of alkene C(sp 3 )−C(sp 2 ) bonds has been an unexplored area for C−C bond formation. Herein 64 examples of β‐alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β‐nitrostyrenes by ozone/Fe II ‐mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso‐moracin and the drug ( E )‐metanicotine.