Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis

Journal of the American Chemical Society

Volumn 138, Issue 27, 2016, Pages 8372-8375

  Friis, Stig D ^a   Pirnot, Michael T ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG PRODUCTS; STYRENE;

ARYL BROMIDES; ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLES; HYDROARYLATION; NATURAL PRODUCTS; PALLADIUM CATALYSIS; PHARMACEUTICAL DRUGS; SYNERGISTIC COMBINATIONS;

CATALYSIS;

BROMIDE; COPPER; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; VINYLARENE; ALKENE; AROMATIC HYDROCARBON;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; HYDROGENATION; REACTION TIME; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; CHEMISTRY;

ALKENES; CATALYSIS; COPPER; HYDROCARBONS, AROMATIC; PALLADIUM;

EID: 84978803498     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b04566     Document Type: Article

References (51)

1. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417 10.1021/cr100327p
2. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons, Inc.: New York, 2002; pp 215-994.
3. Gligorich, K. M.; Cummings, S. A.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 14193 10.1021/ja076746f
4. Iwai, Y.; Gligorich, K. M.; Sigman, M. S. Angew. Chem., Int. Ed. 2008, 47, 3219 10.1002/anie.200705317
5. Gligorich, K. M.; Iwai, Y.; Cummings, S. A.; Sigman, M. S. Tetrahedron 2009, 65, 5074 10.1016/j.tet.2009.03.096
6. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062 10.1002/anie.200902015
7. Saxena, A.; Choi, B.; Lam, H. W. J. Am. Chem. Soc. 2012, 134, 8428 10.1021/ja3036916
8. Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 10830 10.1002/anie.201304365
9. Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 15746 10.1021/ja4092819
10. Pirnot, M. T.; Wang, Y. M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2016, 55, 48 10.1002/anie.201507594
11. Ito, H.; Kosaka, Y.; Nonoyama, K.; Sasaki, Y.; Sawamura, M. Angew. Chem., Int. Ed. 2008, 47, 7424 10.1002/anie.200802342
12. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234 10.1021/ja9089928
13. Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2013, 135, 2635 10.1021/ja3104582
14. Sakae, R.; Hirano, K.; Miura, M. J. Am. Chem. Soc. 2015, 137, 6460 10.1021/jacs.5b02775
15. McRae, A. L.; Brady, K. T. Expert Opin. Pharmacother. 2001, 2, 883 10.1517/14656566.2.5.883
16. Heydorn, W. E. Expert Opin. Invest. Drugs 1999, 8, 417 10.1517/13543784.8.4.417
17. Hills, C. J.; Winter, S. A.; Balfour, J. A. Drugs 1998, 55, 813 10.2165/00003495-199855060-00008
18. Lewis, C. A.; Gustafson, J. L.; Chiu, A.; Balsells, J.; Pollard, D.; Murry, J.; Reamer, R. A.; Hansen, K. B.; Miller, S. J. J. Am. Chem. Soc. 2008, 130, 16358 10.1021/ja807120z
19. Abad, A.; López-Pérez, J. L.; del Olmo, E.; García-Fernández, L. F.; Francesch, A.; Trigili, C.; Barasoain, I.; Andreu, J. M.; Díaz, J. F.; San Feliciano, A. J. Med. Chem. 2012, 55, 6724 10.1021/jm2017573
20. Swift, E. C.; Jarvo, E. R. Tetrahedron 2013, 69, 5799 10.1016/j.tet.2013.05.001
21. Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587 10.1021/acs.chemrev.5b00162
22. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024 10.1021/ja8094075
23. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389 10.1021/ja108547u
24. Zhou, Q.; Srinivas, H. D.; Dasgupta, S.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 3307 10.1021/ja312087x
25. Yonova, I. M.; Johnson, A. G.; Osborne, C. A.; Moore, C. E.; Morrissette, N. S.; Jarvo, E. R. Angew. Chem., Int. Ed. 2014, 53, 2422 10.1002/anie.201308666
26. Konev, M. O.; Hanna, L. E.; Jarvo, E. R. Angew. Chem., Int. Ed. 2016, 55, 6730 10.1002/anie.201601206
27. Do, H.-Q.; Chandrashekar, E. R. R.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 16288 10.1021/ja408561b
28. Woodmansee, D. H.; Pfaltz, A. Chem. Commun. 2011, 47, 7912 10.1039/c1cc11430a
29. Tolstoy, P.; Engman, M.; Paptchikhine, A.; Bergquist, J.; Church, T. L.; Leung, A. W.-M.; Andersson, P. G. J. Am. Chem. Soc. 2009, 131, 8855 10.1021/ja9013375
30. Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850 10.1021/ja053270w
31. For a report that includes computational studies on the proclivity of various alkene substrates to undergo hydrocupration with a SEGPHOS-based CuH catalyst, see: Yang, Y.; Shi, S.-L.; Niu, D.; Liu, P.; Buchwald, S. L. Science 2015, 349, 62 10.1126/science.aab3753
32. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467 10.1016/S0040-4039(00)91094-3
33. Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1981, 22, 959 10.1016/0040-4039(81)89020-X
34. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359 10.1021/jo00306a012
35. Huang, J.; Chan, J.; Chen, Y.; Borths, C. J.; Baucom, K. D.; Larsen, R. D.; Faul, M. M. J. Am. Chem. Soc. 2010, 132, 3674 10.1021/ja100354j
36. Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084 10.1039/c1cs15071e
37. Nahra, F.; Macé, Y.; Lambin, D.; Riant, O. Angew. Chem., Int. Ed. 2013, 52, 3208 10.1002/anie.201208612
38. Vercruysse, S.; Cornelissen, L.; Nahra, F.; Collard, L.; Riant, O. Chem.-Eur. J. 2014, 20, 1834 10.1002/chem.201304284
39. Nahra, F.; Macé, Y.; Boreux, A.; Billard, F.; Riant, O. Chem.-Eur. J. 2014, 20, 10970 10.1002/chem.201404015
40. Ratniyom, J.; Dechnarong, N.; Yotphan, S.; Kiatisevi, S. Eur. J. Org. Chem. 2014, 2014, 1381 10.1002/ejoc.201301634
41. Semba, K.; Nakao, Y. J. Am. Chem. Soc. 2014, 136, 7567 10.1021/ja5029556
42. Smith, K. B.; Logan, K. M.; You, W.; Brown, M. K. Chem.-Eur. J. 2014, 20, 12032 10.1002/chem.201404310
43. Logan, K. M.; Smith, K. B.; Brown, M. K. Angew. Chem., Int. Ed. 2015, 54, 5228 10.1002/anie.201500396
44. Jia, T.; Cao, P.; Wang, B.; Lou, Y.; Yin, X.; Wang, M.; Liao, J. J. Am. Chem. Soc. 2015, 137, 13760 10.1021/jacs.5b09146
45. Semba, K.; Ariyama, K.; Zheng, H.; Kameyama, R.; Sakaki, S.; Nakao, Y. Angew. Chem., Int. Ed. 2016, 55, 6275 10.1002/anie.201511975
46. For computational studies exploring the regioselectivity of alkene insertion with analogous Cu(I) boryl complexes, see: Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Organometallics 2007, 26, 2824 10.1021/om070103r
47. For a study regarding alkene insertion of stoichiometric Cu(I) boryl complexes, see: Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405 10.1021/om060131u
48. Tsuda, T.; Hashimoto, T.; Saegusa, T. J. Am. Chem. Soc. 1972, 94, 658 10.1021/ja00757a069
49. Wang, Y.-M.; Bruno, N. C.; Placeres, á. L.; Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 10524 10.1021/jacs.5b07061
50. Trimethylsilanoate bases have previously been found to be efficient bases in Pd-catalyzed cross-coupling chemistry. For a representative example, see: Denmark, S. E.; Tymonko, S. J. Org. Chem. 2003, 68, 9151 10.1021/jo0351771
51. Deuterium labeling and computational studies for the CuH-catalyzed hydroboration of styrene derivatives indicate that hydrocupration occurs through cis-addition, and boryl transmetalation is stereoretentive. The sense of stereoinduction with (R)-DTBM-SEGPHOS for CuH-catalyzed hydroboration, hydroamination, and hydroarylation is the same; see ref 3d and the following: Noh, D.; Yoon, S. K.; Won, J.; Lee, J. Y.; Yun, J. Chem.-Asian J. 2011, 6, 1967 10.1002/asia.201100146