Di-p-nitrobenzyl azodicarboxylate (DNAD): An alternative azo-reagent for the Mitsunobu reaction

Tetrahedron

Volumn 67, Issue 7, 2011, Pages 1456-1462

  Yang, Jianhai ^a   Dai, Liyan ^a   Wang, Xiaozhong ^a   Chen, Yingqi ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Azo reagent; DNAD; Mitsunobu reaction; Separation friendly

Indexed keywords

ALCOHOL; AZO COMPOUND; DI 4 NITROBENZYL AZODICARBOXYLATE; DIISOPROPYL AZODICARBOXYLATE; HYDRAZINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; FILTRATION; MITSUNOBU REACTION; OXIDATION; PRIORITY JOURNAL;

EID: 78951493586     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.036     Document Type: Article

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27. 3 (1.05 equiv), and azo-reagent (1.05 equiv) were added to the reaction mixture sequentially. The mixture was stirred for about another 6 h at the same temperature. The mixture was cooled and the hydrazine precursor was separated directly from the reaction mixture via filtration. Then the mixture was treated with saturated sodium chloride, and extracted with dichloromethane. The combined organic layer was then washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. Flash silica gel chromatography gave the pure product.