NDLI: Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents

Content Provider	Royal Society of Chemistry (RSC)
Author	Taniguchi, Tsuyoshi Hirose, Daisuke Košmrlj, Janez Gazvoda, Martin
Copyright Year	2016
Abstract	Ethyl 2-arylhydrazinecarboxylates can work as organocatalysts for Mitsunobu reactions because they provide ethyl 2-arylazocarboxylates through aerobic oxidation with a catalytic amount of iron phthalocyanine. First, ethyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate has been identified as a potent catalyst, and the reactivity of the catalytic Mitsunobu reaction was improved through strict optimization of the reaction conditions. Investigation of the catalytic properties of ethyl 2-arylhydrazinecarboxylates and the corresponding azo forms led us to the discovery of a new catalyst, ethyl 2-(4-cyanophenyl)hydrazinecarboxylates, which expanded the scope of substrates. The mechanistic study of the Mitsunobu reaction with these new reagents strongly suggested the formation of betaine intermediates as in typical Mitsunobu reactions. The use of atmospheric oxygen as a sacrificial oxidative agent along with the iron catalyst is convenient and safe from the viewpoint of green chemistry. In addition, thermal analysis of the developed Mitsunobu reagents supports sufficient thermal stability compared with typical azo reagents such as diethyl azodicarboxylate (DEAD). The catalytic system realizes a substantial improvement of the Mitsunobu reaction and will be applicable to practical synthesis.
Starting Page	5148
Ending Page	5159
Page Count	12
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	8
Journal	Chemical Science
DOI	10.1039/c6sc00308g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Phthalocyanine Azo compound Oxygen Diethyl azodicarboxylate Program optimization Betaine Mitsunobu reaction Green chemistry Mitsunobu Thermal analysis Ethyl Nucleophile
Content Type	Text
Resource Type	Article
Subject	Chemistry

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