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Synfacts 2010(3): 0371-0371  
DOI: 10.1055/s-0029-1219284
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem One-Pot Diazo Transfer-Click Reactions Using Cu/C as a Catalyst

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
C.-T. Lee, S. Huang, B. H. Lipshutz*
University of California, Santa Barbara, USA
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

Tandem one-pot diazo transfer-click reactions promoted by a heterogeneous Cu/C catalyst were described. Azide compounds 3 were readily prepared in situ from the corresponding amines 1 (1.5 mmol) and trifluoro-­methanesulfonyl azide 2 (TfN3; 1.5 mmol) in the presence of Cu/C (0.09 mmol) and Ba(OH)2 (1.5 mmol) via diazo transfer reaction. After completion of the diazo transfer, alkynes 4 (0.75 mmol) and triethylamine (1.4 mmol) were added to give the desired ‘click’ products 5 (10 examples, 72-99% yield).