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 Title/Abstract Full Text View citing articles Show Details Muchowski, Joseph M.; Solas, Dennis R. Tetrahedron Letters, 1983 , vol. 24, # 33 p. 3455 - 3456

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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 ...