Photoredox-Catalyzed Hydroxymethylation of Heteroaromatic Bases

Journal of Organic Chemistry

Volumn 81, Issue 16, 2016, Pages 6980-6987

  Huff, Chelsea A ^a   Cohen, Ryan D ^a   Dykstra, Kevin D ^a   Streckfuss, Eric ^a   DiRocco, Daniel A ^a   Krska, Shane W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

HETEROARENES; HYDROXYMETHYLATION; PHOTOREDOX CATALYSIS; VISIBLE LIGHT;

CATALYSIS;

CATALYSIS; LIGHT; ROOM TEMPERATURE;

EID: 84983372336     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b00811     Document Type: Article

References (27)

1. Cernak, T.; Dykstra, K. D.; Tyagarajan, S.; Vachal, P.; Krska, S. W. Chem. Soc. Rev. 2016, 45, 546 10.1039/C5CS00628G
2. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369 10.1038/nchem.1607
3. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960 10.1002/anie.201201666
4. Duncton, M. A. MedChemComm 2011, 2, 1135 10.1039/c1md00134e
5. Sloan, K. B.; Bodor, N. Int. J. Pharm. 1982, 12, 299 10.1016/0378-5173(82)90101-6
6. Buratti, W.; Gardini, G. P.; Minisci, F. Tetrahedron 1971, 27, 3655 10.1016/S0040-4020(01)97776-2
7. Ishida, A.; Toki, S.; Takamuku, S. J. Chem. Soc., Chem. Commun. 1985, 1481 10.1039/c39850001481
8. Minisci, F.; Vismara, E.; Fontana, F.; Morini, G.; Serravalle, M.; Giordano, C. J. Org. Chem. 1986, 51, 4411 10.1021/jo00373a013
9. Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gambarotti, C.; Pruna, B.; Pierini, M.; Fontana, F. Synlett 2004, 874 10.1055/s-2004-820013
10. Neubert, T. D.; Schmidt, Y.; Conroy, E.; Stamos, D. Org. Lett. 2015, 17, 2362 10.1021/acs.orglett.5b00861
11. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
12. Reckenthäler, M.; Griesbeck, A. G. Adv. Synth. Catal. 2013, 355, 2727 10.1002/adsc.201300751
13. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
14. DiRocco, D. A.; Dykstra, K.; Krska, S.; Vachal, P.; Conway, D. V.; Tudge, M. Angew. Chem., Int. Ed. 2014, 53, 4802 10.1002/anie.201402023
15. Jin, J.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565 10.1002/anie.201410432
16. Ambala, S.; Thatikonda, T.; Sharma, S.; Munagala, G.; Yempalla, K. R.; Vishwakarma, R. A.; Singh, P. P. Org. Biomol. Chem. 2015, 13, 11341 10.1039/C5OB01268F
17. Devari, S.; Shah, B. A. Chem. Commun. 2016, 52, 1490 10.1039/C5CC08817H
18. Heteroaromatic systems were selected based on their prevalence in pharmaceuticals. See: Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845 10.1021/jm4017625
19. A mechanism involving trapping of an incipient arene radical cation is plausible; see: Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326 10.1126/science.aac9895
20. Rao, H.; Wang, P.; Li, C.-J. Eur. J. Org. Chem. 2012, 6503 10.1002/ejoc.201201093
21. Inuki, S.; Sato, K.; Fujimoto, Y. Tetrahedron Lett. 2015, 56, 5787 10.1016/j.tetlet.2015.09.012
22. Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87 10.1038/nature14885
23. Ochiai, M.; Morita, K. Tetrahedron Lett. 1967, 8, 2349 10.1016/S0040-4039(00)71604-2
24. Stermitz, F. R.; Wei, C. C.; Huang, W. H. Chem. Commun. (London) 1968, 482 10.1039/c19680000482
25. Henry, L.; Connolly, J. S. J. Am. Chem. Soc. 1968, 90, 2979 10.1021/ja01013a054
26. Evans, B.; Wolfenden, R. J. Am. Chem. Soc. 1970, 92, 4751 10.1021/ja00718a056
27. Ono, I.; Hata, N. Bull. Chem. Soc. Jpn. 1987, 60, 2891 10.1246/bcsj.60.2891