Thioetherification via Photoredox/Nickel Dual Catalysis

Organic Letters

Volumn 18, Issue 4, 2016, Pages 876-879

  Jouffroy, Matthieu ^a   Kelly, Christopher B ^a   Molander, Gary A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; NICKEL; SILICATE; SULFIDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ESTERIFICATION; OXIDATION REDUCTION REACTION;

CATALYSIS; ESTERIFICATION; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; NICKEL; OXIDATION-REDUCTION; SILICATES; SULFIDES;

EID: 84959132380     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00208     Document Type: Article

References (45)

1. Douglas, J. J.; Nguyen, J. D.; Cole, K. P.; Stephenson, C. R. J. Aldrichimica Acta 2014, 47, 15
2. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617 10.1021/jo202538x
3. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
4. Hopkinson, M. N.; Sahoo, B.; Li, J.-L.; Glorius, F. Chem.-Eur. J. 2014, 20, 3874 10.1002/chem.201304823
5. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433 10.1126/science.1253647
6. Zuo, Z. W.; Ahneman, D. T.; Chu, L. L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437 10.1126/science.1255525
7. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566 10.1021/ja208068w
8. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034 10.1021/ja301553c
9. Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505 10.1021/ja400311h
10. Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2015, 137, 2195 10.1021/ja512946e
11. Karakaya, I.; Primer, D. N.; Molander, G. A. Org. Lett. 2015, 17, 3294 10.1021/acs.orglett.5b01463
12. El Khatib, M.; Serafim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254 10.1002/anie.201506147
13. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170 10.1002/chem.201200050
14. Shu, X. Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844 10.1021/ja500716j
15. Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624 10.1021/ja511913h
16. Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929 10.1002/anie.201501908
17. Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11938 10.1021/jacs.5b08304
18. Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 475 10.1021/jacs.5b10963
19. Corce, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Angew. Chem., Int. Ed. 2015, 54, 11414 10.1002/anie.201504963
20. Matsuoka, D.; Nishigaichi, Y. Chem. Lett. 2014, 43, 559 10.1246/cl.131132
21. Matsuoka, D.; Nishigaichi, Y. Chem. Lett. 2015, 44, 163 10.1246/cl.140940
22. Tian, Z.; Fattahi, A.; Lis, L.; Kass, S. R. J. Am. Chem. Soc. 2006, 128, 17087 10.1021/ja065348u
23. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255 10.1021/ar020230d
24. Huston, P.; Espenson, J. H.; Bakac, A. J. Am. Chem. Soc. 1992, 114, 9510 10.1021/ja00050a033
25. Denes, F.; Pichowicz, M.; Povie, G.; Renaud, P. Chem. Rev. 2014, 114, 2587 10.1021/cr400441m
26. Tasker, S. Z.; Jamison, T. F. J. Am. Chem. Soc. 2015, 137, 9531 10.1021/jacs.5b05597
27. Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330 10.1038/nature14875
28. He, Y.; Wu, H.; Toste, F. D. Chem. Sci. 2015, 6, 1194 10.1039/C4SC03092C
29. Xuan, J.; Zeng, T.-T.; Chen, J.-T.; Lu, L.-Q.; Xiao, W. J. Chem.-Eur. J. 2015, 21, 4962 10.1002/chem.201500227
30. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596 10.1021/cr100347k
31. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180 10.1021/ja0580340
32. Fernández-Rodríguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663 10.1021/jo802594d
33. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534 10.1021/ar800098p
34. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598 10.1021/ja00151a033
35. Peach, M. E. In The Chemistry of the Thiol Group; Patai, S., Ed.; John Wiley & Sons: London, 1974; pp 721-784.
36. Yin, J.; Pidgeon, C. Tetrahedron Lett. 1997, 38, 5953 10.1016/S0040-4039(97)01352-X
37. Beletskaya, I. P.; Ananikov, D. P. Chem. Rev. 2011, 111, 1596 10.1021/cr100347k
38. Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590 10.3390/molecules16010590
39. Bichler, P.; Love, J. A. Top. Organomet. Chem. 2010, 31, 39 10.1007/978-3-642-12073-2-3
40. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205 10.1021/cr9902749
41. Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896 10.1021/ja513079r
42. Straathof, N. J. W.; Tegelbeckers, B. J. P.; Hessel, V.; Wang, X.; Noël, T. Chem. Sci. 2014, 5, 4768 10.1039/C4SC01982B
43. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L
44. Vinogradova, E. V.; Zhang, C.; Spokoyny, A. M.; Pentelute, B. L.; Buchwald, S. L. Nature 2015, 526, 687 10.1038/nature15739
45. Although not explicitly shown in Scheme 5, attempts to employ electron-rich aryl bromides with these three thiols were not met with success.