Electrolysis as an efficient key step in the homogeneous polymer-supported synthesis of N-substituted pyrroles.
[reaction: see text]. An efficient and general route to the soluble polymer-assisted synthesis of a set of 14 different N-substituted pyrroles using dendritic polyglycerol as a high-loading support is presented. The transformation of furan to the key intermediate 2,5-dialkoxytetrahydrofuran was performed by electrochemical oxidation followed by catalytic hydrogenation with Pt/C in high yield. Both reactions required heterogeneous reagents which can be conveniently used with polyglycerol as a soluble support.
Nad
Sukanya
S
Organische Chemie, Universität Dortmund, Otto-Hahn-Str. 6, D-44227 Dortmund, Germany.
Roller
Sebastian
S
Haag
Rainer
R
Breinbauer
Rolf
R
D004572:Electrolysis / Q000379:methods*; D005663:Furans / Q000737:chemistry*; D005990:Glycerol / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis*
D005663:Furans; D011108:Polymers; D011758:Pyrroles; C043941:polyglycerol; D005990:Glycerol