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Synfacts 2015; 11(4): 0441
DOI: 10.1055/s-0034-1380492
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Flow-Generated Diazo Compounds and Their Use in Cross-Coupling

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Heeyoel Baek
Tran DN, Battilocchio C, Lou S.-B, Hawkins JM, Ley SV * University of Cambridge, UK; Pfizer Worldwide Research and Development, Groton, USA
Flow Chemistry as a Discovery Tool to Access sp2–sp3 Cross-Coupling Reactions via Diazo Compounds.

Chem. Sci. 2015;
6: 1120-1125
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Further Information

Publication History

Publication Date:
18 March 2015 (online)

 
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Key words

diazo compounds - flow reaction - cross-coupling - manganese oxide

Significance

Unstable diazo compounds were generated as reactive intermediates in a flow system using a MnO2-packed cartridge with Hünig’s base. The resulting diazo compounds reacted with carboxylic acids and arylboronic acids under flow conditions to give the corresponding esters 2a–f in 72–100% yield and the C–C coupling products 3a–f in 67–95% yield, respectively.


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Comment

The generated diazo compounds were detected and titrated by in-line IR spectroscopy. The MnO2-packed cartridge was regenerated by flowing tert-butyl hydroperoxide in dichloromethane and reused twice with a slight loss of activity.


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