Organocatalyzed Selective C-D/C-H Exchange Reactions in Conjugated Triene

Author(s): Isao Yamaguchi , Mikihiko Minamitani .

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 3 , 2015

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Graphical Abstract:


The reaction of N-(2,4-dinitrophenyl)pyridinium-d5 chloride with N-(4-methylphenyl)piperazine in refluxing ethanol led to the ring opening of the pyridinium-d5 ring to afford the conjugated triene with a penta-2,4- dienylideneammonium-d5 (PDA-d5) group, namely, triene-Da2Db2Dc. The reaction of triene-Da2Db2Dc with 1,1,2,2- tetracyanoethylene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) in methanol (MeOH) and N,N-dimethylformamide (DMF) selectively activated the C-D bonds at the 2- and 4-positions of the PDA-d5 group. The present selective C-D/C-H exchange reaction may have applications in the development of new organocatalyzed coupling reactions

Keywords: Organocatalyst, C-D/C-H exchange, conjugated triene, pyridinium salt, TCNE, TCNQ.

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Article Details

Year: 2015
Page: [181 - 186]
Pages: 6
DOI: 10.2174/1570178612666141230234619
Price: $58

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