Transition metal and hydrogen bond donor hybrids: Catalysts for the activation of alkylidene malonates

Chemistry - A European Journal

Volumn 18, Issue 27, 2012, Pages 8310-8314

  Nickerson, David M ^a   Mattson, Anita E ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

alkylidene malonate; catalysis; hydrogen bond donor; organocatalysis; palladacycles

Indexed keywords

ALKYLIDENES; ENHANCED REACTIVITY; HIGH YIELD; HYDROGEN BOND DONORS; MALONATES; NUCLEOPHILIC ATTACK; ORGANOCATALYSIS; PALLADACYCLE CATALYST; PALLADACYCLES;

CATALYSIS; CATALYSTS; METABOLISM; REACTION KINETICS; SCAFFOLDS; THIOUREAS; TRANSITION METALS;

UREA;

EID: 84862737461     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201206     Document Type: Article

References (45)

1. E. Negishi, A. de Meijere, Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley, New York, 2002.
2. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2009. For recent reviews, see
3. Y. Takemoto, Chem. Pharm. Bull. 2010, 58, 593
4. S. J. Connon, S. A. Kavanagh, A. Piccinini, Org. Biomol. Chem. 2008, 6, 1339
5. Z. G. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187
6. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299.
7. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999
8. H. Zhang, Z. Shao, Chem. Soc. Rev. 2009, 38, 2745.
9. I. Ibrahem, A. Cordova, Angew. Chem. 2006, 118, 1986
10. Angew. Chem. Int. Ed. 2006, 45, 1952
11. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496
12. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336.
13. S. S. So, T. J. Auvil, V. J. Garza, A. E. Mattson, Org. Lett. 2012, 14, 444
14. S. S. So, J. A. Burkett, A. E. Mattson, Org. Lett. 2011, 13, 716.
15. M. P. Hughes, M. Y. Shang, B. D. Smith, J. Org. Chem. 1996, 61, 4510
16. M. P. Hughes, B. D. Smith, J. Org. Chem. 1997, 62, 4492.
17. M. T. Robak, M. Trincado, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 15110
18. M. Ganesh, D. Seidel, J. Am. Chem. Soc. 2008, 130, 16464
19. C. R. Jones, G. D. Pantos, A. J. Morrison, M. D. Smith, Angew. Chem. 2009, 121, 7527
20. Angew. Chem. Int. Ed. 2009, 48, 7391.
21. W. Zhuang, T. Hansen, K. A. Jorgensen, Chem. Commun. 2001, 347
22. J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030
23. K. A. Jorgensen, Synthesis 2003, 7, 1117
24. J. Zhou, Y. Tang, Chem. Commun. 2004, 432
25. J. Zhou, M. C. Ye, Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309
26. S. Yamazaki, Y. Iwata, J. Org. Chem. 2006, 71, 739
27. Y. Sun, N. Li, Z. Zheng, L. Liu, Y. Yu, Z. Qin, B. Fun, Adv. Synth. Catal. 2009, 351, 3113
28. Y. Liu, D. Shang, X. Zhou, X. Liu, X. Feng, Chem. Eur. J. 2009, 15, 2055
29. Y. Liu, X. Zhou, D. Shang, X. Liu, X. Feng, Tetrahedron 2010, 66, 1447
30. L. Wen, Q. Shen, X. Wan, L. Lu, J. Org. Chem. 2011, 76, 2282.
31. T. Okino, Y. Hoashi, T. Furukawa, X. N. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119
32. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734
33. Angew. Chem. Int. Ed. 2005, 44, 6576
34. K. L. Kimmel, J. D. Weaver, J. A. Ellman, Chem. Sci. 2012, 3, 121.
35. T. Inokuma, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2006, 128, 9413
36. Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. 2005, 117, 4100
37. Angew. Chem. Int. Ed. 2005, 44, 4032
38. P. R. Schreiner, A. Wittkopp, Org. Lett. 2002, 4, 217.
39. C.-L. Cao, Z.-L. Sun, J.-L. Zhou, Y. Tong, J. Org. Chem. 2007, 72, 4073
40. M. Chiarucci, M. Lombardo, C. Trombini, A. Quintavalla, Adv. Synth. Catal. 2012, 354, 364.
41. J. Vicente, J. Abad, J. Lopez-Serrano, P. G. Jones, C. Najera, L. Botella-Segura, Organometallics 2005, 24, 5044.
42. A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407.
43. M. C. Etter, Z. Urbanczyk-Lipkowska, M. Ziaebrahimi, T. W. Panunto, J. Am. Chem. Soc. 1990, 112, 8415.
44. J. Liu, Z. Yang, X. Liu, Z. Wang, Y. Liu, S. Bai, L. Lin, X. Feng, Org. Biomol. Chem. 2009, 7, 4120
45. D. R. Magar, C. Chang, T.-F. Ting, K. Chen, Eur. J. Org. Chem. 2010, 2062.