Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 16, Pages 8926-8935Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01146
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Funding
- National Institutes of Health [AG002132, AG031220]
- Daiichi Sankyo (Tokyo, Japan)
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The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.
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