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Development of a robust immobilized organocatalyst for the redox-neutral mitsunobu reaction†
Leijie Zhou,Stefania Perulli,Marco M. Mastandrea,Patricia Llanes,Junshan Lai
Green Chemistry Pub Date : 10/20/2021 00:00:00 , DOI:10.1039/D1GC02819G
Abstract

A polystyrene-supported version of the Denton catalyst for redox-neutral Mitsunobu reactions, (2-hydroxybenzyl)diphenylphosphine oxide, has been developed and used in catalytic inversion of enantiopure secondary alcohols (21 examples, up to 97% yield and 98% ee) with 2-nitrobenzoic and 2,4-dinitrobenzoic acids. The use in the reaction of alternative pronucleophiles has also been explored (8 successful and 3 unsuccessful examples). The functional resin shows high recyclability (10 cycles, 30 days operation) and can be re-activated by simple treatment with butylamine with further extension of its useful life.

Graphical abstract: Development of a robust immobilized organocatalyst for the redox-neutral mitsunobu reaction
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