Functionalization of Styrenes by Copper-Catalyzed Borylation/ ortho-Cyanation and Silver-Catalyzed Annulation Processes

Angewandte Chemie
Wanxiang Zhao, John Montgomery

Abstract

An efficient two-step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2 pin2 ) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cyanation of the benzene unit. The products thus obtained are further functionalized by a AgNO3 /Selectfluor-mediated coupling of the BPin and cyano functionalities to annulate a new five-membered ring. This combined two-step sequence provides a versatile method for the site-selective derivatization of a broad range of vinyl arene substrates.

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Citations

Jul 20, 2016·Chemical Reviews·Emily C NeeveTodd B Marder
Jul 21, 2016·Journal of the American Chemical Society·Wanxiang Zhao, John Montgomery
Apr 19, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·M R Ranga PrabhathPallavi Sharma
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Oct 28, 2020·Organic Letters·Annabel Q Ansel, John Montgomery
Sep 28, 2017·Organic Letters·Chenhui ChenZhan Lu
Jun 6, 2017·The Journal of Organic Chemistry·Xinju ZhuXin-Qi Hao

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