Synthesis 2012; 44(15): 2436-2440
DOI: 10.1055/s-0032-1316553
paper
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Pentafluorophenylation of Nitroalkenes

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
› Author Affiliations
Further Information

Publication History

Received: 17 April 2012

Accepted after revision: 22 May 2012

Publication Date:
27 June 2012 (online)


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.

 
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