A synthesis of 3-substituted pyrroles through the halogen-metal exchange reaction of 3-bromo-1-(triisopropylsilyl) pyrrole

Alan P. Kozikowski, Xue Min Cheng

Research output: Contribution to journalArticle

Abstract

In our efforts to develop new, practical entries to several unique classes of indole-containing natural products, we needed to develop a method for achieving selective functionalization of the β-position of pyrrole. While interaction of pyrrole with an electrophilic agent generally leads to introduction of a new group into its α-position,1 it has been demonstrated recently that protection of the pyrrole ring nitrogen with a phenylsulfonyl group2 or the bulky triisopropylsilyl group3 can lead to substitution at the βposition. Thus, while NBS reacts with the N-tert-butyldiphenylsilyl derivative of pyrrole to give a mixture of bromopyrroles,4 n-triisopropylsilyl derivative 1 gives predominantly the corresponding 3-bromo derivative 2.3.

Original languageEnglish (US)
Pages (from-to)3239-3240
Number of pages2
JournalJournal of Organic Chemistry
Volume49
Issue number17
DOIs
StatePublished - Feb 1984

ASJC Scopus subject areas

  • Organic Chemistry

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