Di-p-nitrobenzyl azodicarboxylate (DNAD): an alternative azo-reagent for the Mitsunobu reaction |
| |
Authors: | Jianhai YangLiyan Dai Xiaozhong WangYingqi Chen |
| |
Affiliation: | Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, PR China |
| |
Abstract: | Di-p-nitrobenzyl azodicarboxylate is prepared in 83.6% yield in two steps as a bright yellow solid, which can be used as an azo-reagent in the Mitsunobu reaction. When a chiral secondary alcohol was used, sufficient configurational inversion of alcohol occurred under Mitsunobu conditions. That the hydrazine produced from DNAD is semisoluble in some solvents such as THF and CH2Cl2 makes it separated easily from the reaction mixture just via filtration. Then the recovered hydrazine compound can be re-exposed to oxidant to produce DNAD. Because DNAD is more stable than DIAD at ambient temperatures and allows easy separation, it is a good alternative azo-reagent for the Mitsunobu reaction. |
| |
Keywords: | DNAD Mitsunobu reaction Azo-reagent Separation-friendly |
本文献已被 ScienceDirect 等数据库收录! |