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Synthesis of nitrophenyl and fluorophenyl azides and diazides by S N Ar under phase‐transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents
Author(s) -
Leyva Elisa,
Aguilar Johana,
GonzálezBalderas Regina M.,
VegaRodríguez Sarai,
LoredoCarrillo Silvia E.
Publication year - 2021
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4171
Subject(s) - chemistry , aryl , sodium azide , click chemistry , azide , reagent , microwave irradiation , combinatorial chemistry , alkyl , photochemistry , medicinal chemistry , organic chemistry , catalysis
Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a S N Ar substitution on halogenated benzenes with a phase‐transfer catalyst ( PTC ) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene ( pF ), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron‐withdrawing substituents (COH, COR, COOR, CN, NO 2 , or F). A discussion on the mechanisms and the products obtained in these S N Ar reactions is presented.