N-(triisopropylsilyl) pyrrole. A progenitor" par excellence" of 3-substituted pyrroles

BL Bray, PH Mathies, R Naef, DR Solas…

Index: Bray, Brian L.; Mathies, Peter H.; Naef, Reto; Solas, Dennis R.; Tidwell, Thomas T.; et al. Journal of Organic Chemistry, 1990 , vol. 55, # 26 p. 6317 - 6328

Full Text: HTML

Citation Number: 232

Abstract

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the CY positions. 1- (Triisopropylsily1) pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the 0 position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion ...