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Synfacts 2011(4): 0449-0449  
DOI: 10.1055/s-0030-1259736
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Flow Macrocyclization Using Copper Tubing

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
A. R. Bogdan, K. James*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

Flow macrocyclization with a ­copper surface catalyst via the azide-acetylene cycloaddition reaction was described. The flow macrocyclization of an azidealkyne 1 with TTTA and DIPEA was performed in copper tubing (3 m length, 0.75 mm inner diameter) to give the tri­azole-containing macrocycle 2 in 73% isolated yield within five minutes of residence time without addition of extraneous copper(I) salt in the reaction mixture. The structure of the 12-memberd macrocycle 2 was confirmed by X-ray crystallography.