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Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations.

ABSTRACT: This study examined whether commercially available diazonium salts could be used as efficient aromatic azide precursors in one-pot multi-step click transformations. Seven different diazonium salts, including Fast Red RC, Fast Blue B, Fast Corinth V and Variamine Blue B were surveyed under aqueous click reaction conditions of CuSO(4)/Na ascorbate catalyst with 1:1 t-BuOH:H(2)O solvent. Two-step tandem reactions with terminal alkyne and diyne co-reactants led to 1,2,3-triazole products in 66%-88% yields, while three-step tandem reactions with trimethylsilyl-protected alkyne and diyne co-reactants led to 1,2,3-triazole products in 61%-78% yields.

SUBMITTER: Fletcher JT

PROVIDER: S-EPMC3285242 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations.

Fletcher James T JT Reilly Jacquelline E JE

Tetrahedron letters 20111001 42

This study examined whether commercially available diazonium salts could be used as efficient aromatic azide precursors in one-pot multi-step click transformations. Seven different diazonium salts, including Fast Red RC, Fast Blue B, Fast Corinth V and Variamine Blue B were surveyed under aqueous click reaction conditions of CuSO(4)/Na ascorbate catalyst with 1:1 t-BuOH:H(2)O solvent. Two-step tandem reactions with terminal alkyne and diyne co-reactants led to 1,2,3-triazole products in 66%-88% ...[more]

PMID: 22368306

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