Premium
Triazaphospholenium Tetrafluoroborate: A Phosphorus Analogue of a 1,2,3‐Triazole‐Derived Carbene
Author(s) -
Papke Martin,
Dettling Lea,
Sklorz Julian A. W.,
Szieberth Dénes,
Nyulászi László,
Müller Christian
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709802
Subject(s) - tetrafluoroborate , chemistry , mesoionic , carbene , nucleophile , reagent , phosphorus , cationic polymerization , triazole , alkylation , medicinal chemistry , valence (chemistry) , combinatorial chemistry , organic chemistry , catalysis , ionic liquid
3 H ‐1,2,3,4‐Triazaphosphole derivatives can be selectively alkylated with Meerwein's reagent at the most nucleophilic nitrogen atom. According to the principle of valence isoelectronicity, the corresponding phosphorus heterocycle represents the first formal phosphorus analogue of the well‐known 1,2,3‐triazolylidenes (mesoionic carbenes). Theoretical calculations revealed that the cation in triazaphospholenium tetrafluoroborate is an aromatic system with a high degree of π‐conjugation. First investigations showed that the cationic phosphorus heterocycle can stabilize a [Cu 2 Br 4 ] 2− dianion by formation of a neutral coordination compound with an unusual bonding situation between phosphorus and copper(I).