| Autor: |
O'Brien CJ; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Droege DG; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Jiu AY; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Gandhi SS; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Paras NA; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Olson SH; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States., Conrad J; Institute for Neurodegenerative Diseases (IND), UCSF Weill Institute for Neurosciences , University of California , San Francisco , California 94158 , United States. |
| Abstrakt: |
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. |
