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Potassium Trinitromethanide as a 1,1-Ambiphilic Synthon Equivalent: Access to 2-Nitroarenofurans

Vitaly A. Osyanin*, Dmitry V. Osipov, Maxim R. Demidov and Yuri N. Klimochkin

*Department of Organic Chemistry, Samara State Technical University, 244 Molodogvardeiskaya St., 443100 Samara, Russian Federation, Email: vosyaninmail.ru

V. A. Osyanin, D. V. Osipov, M. R. Demidov, Y. N. Klimochkin, J. Org. Chem., 2014, 79, 1192-1198.

DOI: 10.1021/jo402543s (free Supporting Information)



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Abstract

Potassium trinitromethanide can be used as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine. The method tolerates various functional groups. Formation of an o-quinone methide is postulated as a key intermediate of this cascade process.

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Key Words

Furans


ID: J42-Y2014