Palladium catalyzed asymmetric Suzuki-Miyaura coupling reactions to axially chiral biaryl compounds: Chiral ligands and recent advances

Coordination Chemistry Reviews

Volumn 286, Issue , 2015, Pages 1-16

  Zhang, Dao ^a   Wang, Quanrui ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Asymmetry catalysis; Axially chiral biaryls; Palladium; Suzuki Miyaura coupling

Indexed keywords

EID: 84918841243     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2014.11.011     Document Type: Review

References (69)

1. Bringmann G., Gulder T., Gulder T.A.M., Breuning M. Chem. Rev. 2011, 111:563.
2. Bringmann G., Mortimer A.J.P., Keller P.A., Gresser M.J., Garner J., Breuning M. Angew. Chem. Int. Ed. 2005, 44:5384.
3. Kozlowski M.C., Morgan B.J., Linton E.C. Chem. Soc. Rev. 2009, 38:3193.
4. Genet J.-P., Ayad T., Ratovelomanana-Vidal V. Chem. Rev. 2014, 114:2824.
5. Miyaura N., Suzuki A. Chem. Rev. 1995, 95:2457.
6. Baudoin O. Eur. J. Org. Chem. 2005, 4223.
7. Cammidge A.N., Crépy K.V.L. Chem. Commun. 2000, 1723.
8. Genov M., Almorin A., Espinet P. Chem. Eur. J. 2006, 12:9346.
9. Genov M., Almorin A., Espinet P. Tetrahedron: Asymmetry 2007, 18:625.
10. Audin C., Daran J.-C., Deydier E., Manoury E., Poli R. Comptes Rendus Chimie 2010, 13:890.
11. Bayda S., Cassen A., Daran J.-C., Audin C., Poli R., Manoury E., Deydier E. J. Organomet. Chem. 2014, 772-773:258.
12. Jensen J.F., Johannsen M. Org. Lett. 2003, 5:3025.
13. Yin J., Buchwald S.L. J. Am. Chem. Soc. 2000, 122:12051.
14. Shen X., Jones G.O., Waston D.A., Bhayana B., Buchwald S.L. J. Am. Chem. Soc. 2010, 132:11278.
15. Wang S., Li J., Miao T., Wu W., Li Q., Zhuang Y., Zhou Z., Qiu L. Org. Lett. 2012, 14:1966.
16. Wu W., Wang S., Zhou Y., He Y., Zhuang Y., Li L., Wan P., Wang L., Zhou Z., Qiu L. Adv. Synth. Catal. 2012, 354:2395.
17. Zhou Y., Wang S., Wu W., Li Q., He Y., Zhuang Y., Li L., Pang J., Zhou Z., Qiu L. Org. Lett. 2013, 15:5508.
18. Liu G., Xu G., Luo R., Tang W. Synlett 2013, 24:2465.
19. Tang W., Patel N.D., Xu G., Xu X., Savoie J., Ma S., Hao M.-H., Keshipeddy S., Capacci A.G., Wei X., Zhang Y., Gao J.J., Li W., Rodriguez S., Lu B.Z., Yee N.K., Senanayake C.H. Org. Lett. 2012, 14:2258.
20. Xu G., Fu W., Liu G., Senanayake C.H., Tang W. J. Am. Chem. Soc. 2014, 136:570.
21. Uozumi Y., Matsuura Y., Arakawa T., Yamada Y.M.A. Angew. Chem. Int. Ed. 2009, 48:2708.
22. Sun L., Dai W.-M. Tetrahedron 2011, 67:9072.
23. Castillo A.B., Perandones B.F., Zangrando E., Gladiali S., Godard C., Claver C. J. Organomet. Chem. 2013, 743:31.
24. Kamei T., Sato A.H., Iwasawa T. Tetrahedron Lett. 2011, 52:2638.
25. Jumde V.R., Luliao A. Tetrahedron: Asymmetry 2011, 22:2151.
26. Bronger R.P.J., Guiry P.J. Tetrahedron: Asymmetry 2007, 18:1094.
27. Ros A., Estepa B., Ramírez-López P., Álvarez E., Fernández R., Lassaletta J.M. J. Am. Chem. Soc. 2013, 135:15730.
28. Castanet A.-S., Colobert F., Broutin P.-E., Obringer M. Tetrahedron: Asymmetry 2002, 13:659.
29. Mikami K., Miyamoto T., Hatano M. Chem. Commun. 2004, 2082.
30. Deraedt C., Astruc D. Acc. Chem. Res. 2014, 47:494.
31. Sawai K., Tatumi R., Nakahodo T., Fujihara H. Angew. Chem. Int. Ed. 2008, 47:6917.
32. Bermejo A., Ros A., Fernández R., Lassaletta J.M. J. Am. Chem. Soc. 2008, 130:15798.
33. Ros A., Estepa B., Bermejo A., Álvarez R., Fernández R., Lassaletta J.M. J. Org. Chem. 2012, 77:4740.
34. Zhang S., Wang Z., Xu M., Lin G. Org. Lett. 2010, 23:5546.
35. He X., Zhang S., Guo Y., Wang H., Lin G. Organometallics 2012, 31:2945.
36. Selander N., Szabó K.J. Chem. Rev. 2011, 111:2048.
37. Takemptp T., Iwasa S., Hamada H., Shibatomi K., Kameyama M., Motoyama Y., Nishiyama H. Tetrahedron Lett. 2007, 48:3397.
38. Zhang B., Wang W., Shao D., Hao X., Gong J., Song M. Organometallics 2010, 29:2579.
39. Wang T., Hao X., Huang J., Wang K., Gong J., Song M. Organometallics 2014, 33:194.
40. Würtz S., Glorius F. Acc. Chem. Res. 2008, 41:1523.
41. Díez-Gonzalez S., Marion N., Nolan S.P. Chem. Rev. 2009, 109:3612.
42. Debono N., Labande A., Manoury E., Daran J.-C., Poli R. Organometallics 2010, 29:1879.
43. Loxq P., Debono N., Gülcemal S., Daran J.-C., Manoury E., Poli R., Cetinkaya B., Lababde A. New J. Chem. 2014, 38:338.
44. Wang F., Liu L., Wang C., Shi M. Coord. Chem. Rev. 2012, 256:804.
45. César V., Bellemin-Laponnaz S., Gade L.H. Chem. Soc. Rev. 2004, 33:619.
46. Shi G., Tang J., Zhang D., Wang Q., Chen Z., Weng L. J. Organomet. Chem. 2012, 700:223.
47. Li Y., Tang J., Gu J., Wang Q., Sun P., Zhang D. Organometallics 2014, 33:876.
48. Wu L., Salvador A., Ou A., Shi M.W., Skelton B.W., Dorta R. Synlett 2013, 24:1215.
49. Valente C., Calimsiz S., Hoi K.H., Mallik D., Sayah M., Organ M.G. Angew. Chem. Int. Ed. 2012, 51:2.
50. Benhamou L., Besnard C., Kündig E.P. Organometallics 2014, 33:260.
51. Grach G., Pieters G., Dinut A., Terrasson V., Medimagh R., Bridoux A., Razafimahaleo V., Gaucher A., Marque S., Marrot J., Prim D., Gil R., Planas J.G., Vinas C., Thomas I., Roblin J.-P., Troin Y. Organometallics 2011, 30:4074.
52. Lipshutz B.H., Kayser F., Lui Z.-P. Angew. Chem. Int. Ed. 1994, 33:1842.
53. Colobert F., Valdivia V., Choppin S., Leroux F.R., Fernandez I., Alvarez E., Khiar N. Org. Lett. 2009, 22:5130.
54. Meyers A.I., Nelson T.D., Moorlag H., Rawson D.J., Meier A. Tetrahedron 2004, 60:4459.
55. Nelson T.D., Meyers A.I. Tetrahedron Lett. 1994, 35:3259.
56. Kamikawa K., Watanabe T., Uemura M. J. Org. Chem. 1996, 61:1375.
57. Wilson J.A., Cram D.J. J. Am. Chem. Soc. 1982, 104:881.
58. Li X., Yang J., Kozlowski M. Org. Lett. 2001, 3:1137.
59. Luo Z., Liu Q., Gong L., Cui X., Mi A., Jiang Y. Angew. Chem. Int. Ed. 2002, 41:4532.
60. Hayashi T., Hayashizaki K., Kiyoi T., Ito Y. J. Am. Chem. Soc. 1998, 110:8153.
61. Kano T., Ohyabu Y., Saito S., Yamamoto H. J. Am. Chem. Soc. 2002, 124:5365.
62. Hayashi T., Niizuma S., Kamikawa T., Suzuki N., Uozumi Y. J. Am. Chem. Soc. 1995, 117:9101.
63. Penhoat M., Levachet V., Dupas G. J. Org. Chem. 2003, 68:9517.
64. Bringmann G., Menche D. Acc. Chem. Res. 2001, 34:615.
65. Nishii Y., Wakasugi K., Koga K., Tanabe Y. J. Am. Chem. Soc. 2004, 126:5358.
66. Gutnov A. Angew. Chem. Int. Ed. 2004, 43:3795.
67. Aldemir H., Richarz R., Gulder T.A.M. Angew. Chem. Int. Ed. 2014, 53:8286.
68. Ikezawa N., Iwasa K., Sato F. J. Biol. Chem. 2008, 283:8810.
69. Han F. Chem. Soc. Rev. 2013, 42:5270.