Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition.

Barzanò G; Cheseaux A; Hu X

doi:10.1021/acs.orglett.8b03772

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Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition.

Barzanò G Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
Cheseaux A Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
Hu X Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.

2019-01-10

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Organic letters. - 2019

Physical and Theoretical Chemistry

English Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.

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