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Synfacts 2016; 12(06): 0643
DOI: 10.1055/s-0035-1562167
DOI: 10.1055/s-0035-1562167
Polymer-Supported Synthesis
Sequential C–C Bond Formation via Allylic and Benzylic Boronic Acids
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
17. Mai 2016 (online)
Key words
flow chemistry - C–C bond formation - boronic acids - diazo compounds - iterative synthesis - cascade reactionSignificance
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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