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Cover Feature: Activation of Acetonitrile with (C 2 F 5 ) 3 PF 2 and Amines (Chem. Eur. J. 27/2018)
Author(s) -
Bader Julia,
Neumann Beate,
Stammler HansGeorg,
Ignat'ev Nikolai,
Hoge Berthold
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801145
Subject(s) - acetonitrile , deprotonation , chemistry , triethylamine , moiety , medicinal chemistry , ligand (biochemistry) , nucleophile , amine gas treating , hydroamination , stereochemistry , organic chemistry , catalysis , ion , biochemistry , receptor
Eureka! We found it ! Acetonitrile is not easily activated or even deprotonated. A combination of the strong Lewis acid (C 2 F 5 ) 3 PF 2 and triethylamine, however, are able to deprotonate CH 3 CN. The resulting cyanomethyl function is bound to the phosphorus moiety, affording the highly stable salt [HNEt 3 ][P(C 2 F 5 ) 3 F 2 (CH 2 CN)]. Using more nucleophilic secondary and primary amines instead of NEt 3 leads to a phosphate featuring an amidine ligand, which formally results from hydroamination of acetonitrile by the amine. More information can be found in the Full Paper by B. Hoge et al. on page 6975.