19740-72-8Relevant articles and documents
The effect of acid strength on the Mitsunobu esterification reaction: Carboxyl vs hydroxyl reactivity
Hughes, David L.,Reamer, Robert A.
, p. 2967 - 2971 (1996)
In the presence of carboxylic acids, the adduct formed between triphenylphosphine and diisopropyl azodicarboxylate reacts to form mono- and bis-acylated hydrazides and the carboxylic acid anhydrides. These products are formed via attack of the carboxylate on the triphenylphosphonium group of the adduct, with weaker acids reacting much faster than stronger acids. This provides an explanation for the observation in the literature that acids stronger than acetic acid, such as 4-nitrobenzoic acid and chloroacetic acid, provide better yields in esterification reactions, since reaction of the alcohol with the phosphonium group of the adduct is more rapid than the competing reaction of the carboxylate for the phosphonium group.
1,2-DIALKOXYCARBONYLHYDRAZINE DERIVATIVES OF PYRROLES AND INDOLIZINES. A NEW SYNTHESIS OF CYCLAZINES
Flitsch, Wilhelm,Heinrich, Juergen
, p. 3673 - 3676 (1980)
The reaction of pyrroles 1 with diisopropyl azodicarboxylate 2 yields 2- and 2,5-substituted derivatives. 3- and 1,3-substituted indolizines 5 and 6 are formed by the same route.Cyclazines 7 have been obtained from 5 and 6 with dimethyl acetylenedicarboxylate.
Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light
M?rz,Chudoba,Kohout,Cibulka
supporting information, p. 1970 - 1975 (2017/03/11)
The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.
Copper-catalyzed C-N bond formation using dialkyl azodicarboxylate as the amination reagent
Samzadeh-Kermani, Alireza
, p. 463 - 465 (2016/01/12)
An efficient copper-catalyzed reaction for C-N bond formation using aryl halides, dialkyl azodicarboxylate, and a hydride source is reported. Using this procedure, aryl iodides reacted at ambient conditions, while aryl bromides required heating to 60 °C to accomplish the transformation. Various functional groups were tolerated under the optimum conditions.
