Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins
Dr. Manisha Swain
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorGusein Sadykhov
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorRuoxi Wang
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Ohyun Kwon
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorDr. Manisha Swain
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorGusein Sadykhov
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorRuoxi Wang
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Ohyun Kwon
Department of Chemistry and Biochemistry, University of California—Los Angeles, Los Angeles, CA, 90095-1569 USA
Search for more papers by this authorGraphical Abstract
The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds has been an unexplored area for C−C bond formation. Reported herein are β-alkylated styrene derivatives synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions. The strategy was applied to the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.
Abstract
The dealkenylative alkenylation of alkene C(sp3)−C(sp2) 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/FeII-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.
Conflict of interest
The authors declare no conflict of interest.
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