Premium
N−N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts
Author(s) -
Tota Arianna,
Colella Marco,
Carlucci Claudia,
Aramini Andrea,
Clarkson Guy,
Degennaro Leonardo,
Bull James A.,
Luisi Renzo
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001047
Subject(s) - chemistry , umpolung , electrophile , reagent , nitrogen atom , ammonium , molecule , ammonia , combinatorial chemistry , nitrogen , organic chemistry , nucleophile , ring (chemistry) , catalysis
The formation of hydrazinium salts by N−N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N‐source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X‐ray analysis.