Polyisobutylene-Supported Phosphines as Recyclable and Regenerable Catalysts and Reagents

• Published in: Journal of organic chemistry Vol. 76; no. 16; pp. 6912 - 6917
• Main Authors: Bergbreiter, David E, Yang, Yun-Chin, Hobbs, Christopher E
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 19-08-2011
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Organic chemistry; Organometalloidal and organometallic compounds; P derivatives; Preparations and properties; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Chemical reagent; Separation; Organic phosphine; Mitsunobu reaction; Reuse; Heptane; Supported catalyst; Allylic compound; Chemical reduction; Isobutene polymer; Amination; Aza-Wittig reaction; Acetonitrile; Oxidation; Recycling; Chemical synthesis; Solvent; By product; Catalyst
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo201097x

Phosphines are important as catalysts or reagents in synthesis but must be separated from products after a reaction. This report shows that polyisobutylene (PIB)-bound alkyldiaryl- and triarylphosphines are useful as catalysts in addition and allylic amination reactions or as reagents in aza-Wittig and Mitsunobu reactions. Heptane solutions of such phosphines and their oxidized byproducts can be easily separated from polar solutions of organic products, and PIB-phosphine oxides formed during a reaction can readily be reduced to PIB-phosphines for reuse.