Lithiation Substitution of Unprotected Benzyltetrazoles

Jeff Y. F. Wong, Agnieszka Lewandowska, Benjamin Trowse, Graeme Barker

Research output: Contribution to journalArticle

Abstract

1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.
Original languageEnglish
Pages (from-to)7069-7072
Number of pages4
JournalOrganic Letters
Volume21
Issue number17
Early online date26 Aug 2019
DOIs
Publication statusPublished - 6 Sep 2019

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