C‐F bond activation by saturated NHC: mesoionic compound formation and its unprecedented adduct with B(C6F5)3

TitleC‐F bond activation by saturated NHC: mesoionic compound formation and its unprecedented adduct with B(C6F5)3
Publication TypeJournal Article
Year of Publication2019
AuthorsPait, M, Kundu, G, Tothadi, S, Karak, S, Jain, S, Vanka, K, Sen, SS
JournalAngewandte Chemie - International Edition
Volume58
Issue9
Pagination2804-2808
Date PublishedFEB
Type of ArticleArticle
ISSN1433-7851
KeywordsC-F activation, carbanions, N-heterocyclic carbenes, structure elucidation, Ylides
Abstract

The reaction of SIPr, [1,3‐bis(2,6‐diisopropylphenyl)‐imidazolin‐2‐ylidene] (1), with C6F6 led to the formation of an unprecedented mesoionic compound (2). The formation of 2 is made accessible by deprotonation of the SIPr backbone with simultaneous elimination of HF. The C−F bond para to the imidazolium ring in 2 is only of 1.258(4) Å, which is the one of the shortest structurally authenticated C−F bonds known to date. The liberation of HF during the reaction is unequivocally proved by the addition of one more equivalent of SIPr, which leads to the imidazolium salt with the HF2− anion. To functionalize 2, the latter reacted with B(C6F5)3 to give an unusual donor–acceptor compound, where the fluoride atom from the C6F5 moiety coordinates to B(C6F5)3 and the carbanion moiety remains unaffected. Such coordination susceptibility of the fluoride atom of a nonmetallic system to a main‐group Lewis acid (Fnon‐metal→BR3) is quite unprecedented.

DOI10.1002/anie.201814616
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

12.102

Divison category: 
Catalysis and Inorganic Chemistry
Organic Chemistry
Physical and Materials Chemistry

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