Synthesis of unsymmetrical 1,1 '-disubstituted Bis(1,2,3-triazole)s using monosilylbutadiynes

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Abstract

Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1 -disubstituted-4,4 -linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.
Original languageEnglish
Pages (from-to)537 - 539
Number of pages3
JournalOrganic Letters
Volume13
Issue number3
DOIs
Publication statusPublished - 2011

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