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

Guido Barzanò, Alexis Cheseaux, Xile Hu*

*Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland, Email: xile.huepfl.ch

G. Barzanò, A. Cheseaux, X. Hu, Org. Lett., 2019, 21, 490-493.

DOI: 10.1021/acs.orglett.8b03772 (free Supporting Information)



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Abstract

A Fe-catalyzed addition of alkyl radicals, formed from the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester provides Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides.

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Key Words

vinyl boronates, Zinc


ID: J54-Y2019