Nucleophilic Pentafluorophenylation of Nitroalkenes

Nikolay S. Kondratyev; Artem A. Zemtsov; Vitalij V. Levin; Alexander D. Dilman; Marina I. Struchkova

doi:10.1055/s-0032-1316553

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2436-2440
DOI: 10.1055/s-0032-1316553

paper

Nucleophilic Pentafluorophenylation of Nitroalkenes

Authors

Nikolay S. Kondratyev

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Fax: +7(499)1355328 eMail: adil25@mail.ru
Artem A. Zemtsov

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Fax: +7(499)1355328 eMail: adil25@mail.ru
Vitalij V. Levin

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Fax: +7(499)1355328 eMail: adil25@mail.ru
Alexander D. Dilman*

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Fax: +7(499)1355328 eMail: adil25@mail.ru
Marina I. Struchkova

N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Fax: +7(499)1355328 eMail: adil25@mail.ru

Abstract

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Abstract

The interaction of pentafluorophenylmagnesium bromide with conjugate nitroalkenes is described. The optimized conditions involve performing the reaction either in diethyl ether in the presence of chlorotrimethylsilane or in a tetrahydrofuran–diethyl ether solvent mixture. The addition products can be transformed into 4,5,6,7-tetrafluoroindolines by means of a reduction and cyclization sequence.

Key words

alkenes - nucleophilic addition - fluorine - nitro compounds - pentafluorophenyl

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Referenzen

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