Improved method for the diimide reduction of multiple bonds on solid-supported substrates.
A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron-poor olefins, and terminal alkynes were the most easily reduced.
Buszek
Keith R
KR
Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, Kansas 66506, USA. buszekk@umkc.edu
Brown
Neil
N
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005021:Ethylamines / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012117:Resins, Synthetic / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D005021:Ethylamines; D007094:Imides; D012117:Resins, Synthetic; C016162:triethylamine