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Synfacts 2016; 12(06): 0643
DOI: 10.1055/s-0035-1562167
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Sequential C–C Bond Formation via Allylic and Benzylic Boronic Acids

Contributor(s):
Yasuhiro Uozumi
,
Takuma Sato
Battilocchio C, * Feist F, Hafner A, Simon M, Tran DN, Allwood DM, Blakemore DC, Ley SV. * University of Cambridge and Pfizer Worldwide Medical Chemistry, Cambridge, UK
Iterative Reactions of Transient Boronic Acids Enable Sequential C–C Bond Formation.

Nature Chem. 2016;
8: 360-367
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Further Information

Publication History

Publication Date:
17 May 2016 (online)

 
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Key words

flow chemistry - C–C bond formation - boronic acids - diazo compounds - iterative synthesis - cascade reaction

Significance

Allylic and benzylic boronic acids, prepared in situ from flow-generated diazo compounds and stable boronic acids, were used in sequential C–C bond formation reactions. For example, the sequential reaction of (4-methoxyphenyl)boronic acid with a flow-generated diazo compound and acetaldehyde gave a precursor of the natural product bakuchiol in 60% yield from a single operation.


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Comment

The authors have recently reported the reaction of arylboronic acids with flow-generated diazo compounds (Chem. Sci. 2015, 6, 1120). The current paper describes the sequential formation of up to three C–C bonds.


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