Steric modulation of chiral biaryl diamines via Pd-catalyzed directed C-H arylation

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2613-2615

  Scarborough, Christopher C ^a   McDonald, Richard I ^a   Hartmann, Caroline ^a   Sazama, Graham T ^a   Bergant, Ana ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL GROUPS; ARYL IODIDES; ARYLATION; ASYMMETRIC CATALYSIS; BASIC CONDITIONS; DE PROTECTIONS;

AMINES; AROMATIC COMPOUNDS;

PALLADIUM;

CARBON; DIAMINE DERIVATIVE; HYDROGEN; IODINE DERIVATIVE; PALLADIUM;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CHIRALITY; DEACETYLATION; HALOGENATION; STEREOCHEMISTRY;

CATALYSIS; DIAMINES; HYDROCARBONS, AROMATIC; PALLADIUM;

EID: 64149105444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802632v     Document Type: Article

References (53)

1. 2,2-Diamino-1,1-binaphthyl (DABN) is commercially available. For information regarding the synthesis of diamines in Chart 1, see: (a) Takasaki, M.; Motoyama, Y.; Yoon, S. H.; Mochida, I.; Nagashima, H. J. Org. Chem. 2007, 72, 10291-10293.
2. (b) Korostylev, A.; Tararov, V. I.; Fischer, C.; Monsees, A.; Börner, A. J. Org. Chem. 2004, 69, 3220-3221.
3. (c) Guo, H.; Ding, K. Tetrahedron Lett. 2000, 41, 10061-10064.
4. (d) Gillespie, K. M.; Sanders, C. J.; O'Shaughnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458.
5. (e) Chen, Y. X.; Li, Y. M.; Lam, K. H.; Chan, A. S. C. Chin. J. Chem. 2001, 19, 794-799.
6. Pd-catalyzed aerobic kinetic resolution of secondary alcohols: Chen, T.; Jiang, J. J.; Xu, Q.; Shi, M. Org. Lett. 2007, 9, 865-868.
7. Cu-catalyzed aziridination: (a) Reference 1d.
8. (b) Shi, M.; Wang, C. J. Chirality 2002, 14, 412-416.
9. (c) Gillespie, K. M.; Crust, E. J.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 785-786.
10. (d) Sanders, C. J.; Gillespie, K. M.; Bell, D.; Scott, P. J. Am. Chem. Soc. 2000, 122, 7132-7133.
11. Cu-catalyzed aerobic oxidative coupling of 3-hydroxy-2-naphthoate: Kim, K. H.; Lee, D. W.; Lee, Y. S.; Ko, D. H.; Ha, D. C. Tetrahedron 2004, 60, 9037-9042.
12. Co-catalyzed epoxidation of styrene: Nishinaga, A.; Yamato, H.; Abe, T.; Maruyama, K.; Matsuura, T. Tetrahedron Lett. 1988, 29, 6309-6312.
13. Rh- and Ru-catalyzed hydrogenation: (a) Huang, H.; Okuno, T.; Tsuda, K.; Yoshimura, M.; Kitamura, M. J. Am. Chem. Soc. 2006, 128, 8716-8717.
14. (b) Chen, Y. X.; Li, Y. M.; Lam, K. H.; Chan, A. S. C. Chin. J. Chem. 2003, 21, 66-70.
15. (c) Pérez, C.; Pérez, S.; Fuentes, G. A.; Corma, A. J. Mol. Catal. A: Chem. 2003, 197, 275-281.
16. (d) Chen, Y.-X.; Li, Y.-M.; Lam, K.-H.; Chan, A. S.-C. Chin. J. Chem. 2002, 20, 606-609.
17. (e) Zhang, F. Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337-2342.
18. (f) Zhang, F. Y.; Pai, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808-5809.
19. Rh- and Y-catalyzed hydrosilylation: (a) Xu, Q.; Gu, X.; Liu, S.; Dou, Q.; Shi, M. J. Org. Chem. 2007, 72, 2240-2242.
20. (b) Gountchev, T. I.; Tilley, T. D. Organometallics 1999, 18, 5661-5667.
21. 4: Suda, H.; Motoi, M.; Fujii, M.; Kanoh, S.; Yoshida, H. Tetrahedron Lett. 1979, 4565-4568.
22. Pd-catalyzed allylic alkylation: Chen, X.; Guo, R.; Li, Y.; Chen, G.; Yeung, C. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2004, 15, 213-217.
23. Cu-catalyzed alkynylation of aldimines: Hatano, M.; Asai, T.; Ishihara, K. Tetrahedron Lett. 2008, 49, 379-382.
24. Cu- and Ru-catalyzed cyclopropanation: (a) Sanders, C. J.; Gillespie, K. M.; Scott, P. Tetrahedron: Asymmetry 2001, 12, 1055-1061.
25. (b) Munslow, I. J.; Gillespie, K. M.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 1638-1639.
26. (c) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102-2108.
27. Zr-, Y-, Sm-, and La-catalyzed intramolecular hydroamination of alkenes: (a) Wood, M. C.; Leitch, D. C.; Yeung, C. S.; Kozak, J. A.; Schafer, L. L. Angew. Chem., Int. Ed. 2007, 46, 354-358.
28. (b) Gott, A. L.; Clarke, A. J.; Clarkson, G. J.; Scott, P. Organometallics 2007, 26, 1729-1737.
29. (c) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894-895.
30. (d) O'Shaughnessy, P. N.; Gillespie, K. M.; Knight, P. D.; Munslow, I. J.; Scott, P. Dalton Trans. 2004, 2251-2256.
31. (e) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770-1771.
32. (f) O'Shaughnessy, P. N.; Scott, P. Tetrahedron: Asymmetry 2003, 14, 1979-1983.
33. Dialkylzinc addition to cyclic enones: Hatano, M.; Asai, T.; Ishihara, K. Tetrahedron Lett. 2007, 48, 8590-8594.
34. Diels-Alder cycloadditions: (a) Sakakura, A.; Suzuki, K.; Ishihara, K. Adv. Synth. Catal. 2006, 348, 2457-2465.
35. (b) Kano, T.; Tanaka, Y.; Maruoka, K. Org. Lett. 2006, 8, 2687-2689.
36. Glyoxylate-ene reactions: Mikami, K.; Aikawa, K. Org. Lett. 2002, 4, 99-101.
37. Silylcyanation of aldehydes: Zhou, X. G.; Huang, J. S.; Ko, P. H.; Cheung, K. K.; Che, C. M. J. Chem. Soc.; Dalton Trans. 1999, 3303-3309.
38. Morita-Baylis-Hillman reactions: Shi, M.; Liu, X. G. Org. Lett. 2008, 10, 1043-1046.
39. Oxy-Michael addition reactions: Kano, T.; Tanaka, Y.; Maruoka, K. Tetrahedron 2007, 63, 8658-8664.
40. Henry reactions: Liu, X. G.; Jiang, J. J.; Shi, M. Tetrahedron: Asymmetry 2007, 18, 2773-2781.
41. Scarborough, C. C.; Popp, B. V.; Guzei, I. A.; Stahl, S. S. J. Organomet. Chem. 2005, 690, 6143-6155.
42. (b) Scarborough, C. C.; Grady, M. J. W.; Guzei, I. A.; Gandhi, B. A.; Bunel, E. E.; Stahl, S. S. Angew. Chem., Int. Ed. 2005, 44, 5269-5272.
43. See, for example: (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046-4048.
44. (b) Shabashov, D.; Daugulis, O. J. Org. Chem. 2007, 72, 7720-7725.
45. (c) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330-7331.
46. (d) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066-6067.
47. For an earlier demonstration of related reactivity with alkyl iodides and stoichiometric Pd, see: Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759-5760.
48. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312-2313.
49. The DABN substrate appears to be more reactive and susceptible to side reactions. Efforts to perform reactions with aryl iodides other than PhI typically resulted in lower yields. For example, DZ coupling of N,N?-diacetyl-DABN with 1-iodo-3,5-dimethylbenzene proceeded in 46% yield with complete consumption of starting material (cf. entry 5, Table 1).
50. Partial hydrogenation of DABN to form H8-DABN can be achieved without loss of enantiopurity.
51. (a) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999-1010.
52. (b) Pihko, P. M. Lett. Org. Chem. 2005, 2, 398-403.
53. (c) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3211.