Palladium (II/IV) catalyzed cyclopropanation reactions: scope and mechanism

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3211-3221

  Lyons, Thomas W ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON; CYCLOPROPANE DERIVATIVE; GOLD; KETONE DERIVATIVE; PALLADIUM; PLATINUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOPROPANATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 62049085617     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.107     Document Type: Article

References (76)

1. Trofast J., and Wickberg B. Tetrahedron 33 (1977) 875
2. Koft E.R., and Smith III A.B. J. Am. Chem. Soc. 104 (1982) 2659
3. Brown R.F.C., and Teo P.Y.T. Tetrahedron Lett. 25 (1984) 5585
4. Ichimura M., Ogawa T., Katsumata S., Takahashi K., Takahashi I., and Nakano H. J. Antibiot. 44 (1991) 1045
5. Boger D.L., Garbaccio R.M., and Jin Q. J. Org. Chem. 62 (1997) 8875
6. Kirkland T.A., Colucci J., Geraci L.S., Marx M.A., Schneider M., Kaelin Jr. D.E., and Martin S.F. J. Am. Chem. Soc. 123 (2001) 12432
7. Swain N.A., Brown R.C.D., and Bruton G. J. Org. Chem. 69 (2004) 122
8. Ok T., Jeon A., Lee J., Lim J.H., Hong C.S., and Lee H.S. J. Org. Chem. 72 (2007) 7390
9. Clive D.L.J., and Liu D. J. Org. Chem. 73 (2008) 3078
10. Chavan S.P., Pasapathy K., and Shivasankar K. Synth. Commun. 34 (2004) 397
11. Mamane V., Gress T., Krause H., and Fürstner A. J. Am. Chem. Soc. 126 (2004) 8654
12. Harrak Y., Blaszykowski C., Bernard M., Cariou K., Mainetti E., MourièsDhimane A., Fensterbank L., and Malacria M. J. Am. Chem. Soc. 126 (2004) 8656
13. Luzung M.R., Markham J.P., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 10858
14. For reviews on cycloisomerizations, see:
15. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271
16. Aubert C., Buisine O., and Malacria M. Chem. Rev. 102 (2002) 813
17. Trost B.M., and Krische M.J. Synlett (1998) 1
18. Intramolecular cyclization of diazo compounds has also frequently been used to access bicyclo[3.1.0] and [4.1.0] ring systems. For examples, see:
19. Doyle M.P., and Pieters R.J. J. Am. Chem. Soc. 113 (1991) 1423
20. Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.Y., Liras S., Oalmann C.J., Pieters R.J., Protopopova M.N., Raab C.E., Roos G.H.P., Zhou Q., and Martin S.F. J. Am. Chem. Soc. 117 (1995) 5763
21. Doyle M.P., Peterson C.S., and Parker Jr. D.L. Angew. Chem., Int. Ed. 35 (1996) 1334
22. Böhmer J., Grigg R., and Marchbank J.D. Chem. Commun. (2002) 768
23. For examples, see:
24. Meyer F.E., Parsons P.J., and Meijere A. J. Org. Chem. 56 (1991) 6487
25. Owczarczyk Z., Lamaty F., Vawter E.J., and Negishi E. J. Am. Chem. Soc. 114 (1992) 10091
26. Grigg R., Dorrity M.J., and Malone J.F. Tetrahedron Lett. 31 (1990) 1343
27. Brown A., Grigg R., Ravishankar R., and Thornton-Pett M. Tetrahedron Lett. (1994) 2753
28. Grigg R., and Sridharan V. Tetrahedron Lett. 33 (1992) 7965
29. Grigg R., Rasul R., Redpath J., and Wilson D. Tetrahedron Lett. 37 (1996) 4609
30. Marco-Martínez J., Lòpez-Carrillo V., Buñuel E., Simancas R., and Cárdenas D.J. J. Am. Chem. Soc. 129 (2007) 1874
31. Lu X., Zhu G., and Wang Z. Synlett (1998) 115
32. Wang Z., Zhang Z., and Lu X. Organometallics 19 (2000) 775
33. Zhao L., Lu X., and Xu W. J. Org. Chem. 70 (2005) 4059
34. Zhang Q., Lu X., and Han X. J. Org. Chem. 66 (2001) 7676
35. Zhang Q., Xu W., and Lu X. J. Org. Chem. 70 (2005) 1505
36. For a preliminary account of this work, see:
37. Welbes L.L., Lyons T.W., Cychosz K.A., and Sanford M.S. J. Am. Chem. Soc. 129 (2007) 5836 See also:
38. Tong X., Beller M., and Tse M.K. J. Am. Chem. Soc. 129 (2007) 4906
39. Desai L., and Sanford M.S. Angew. Chem., Int. Ed. 46 (2007) 5737
40. Kalyani D., and Sanford M.S. J. Am. Chem. Soc. 130 (2008) 2150
41. Desai L., Hull K.L., and Sanford M.S. J. Am. Chem. Soc. 126 (2004) 9542
42. For examples, see:
43. Muñiz K., Hövelmann C.H., and Streuff J. J. Am. Chem. Soc. 130 (2008) 763
44. Liu G., and Stahl S.S. J. Am. Chem. Soc. 128 (2006) 7179
45. Bäckvall J.E., and Bjoerkman E.E. J. Org. Chem. 45 (1980) 2893
46. Henry P.M., Davies M., Gerguson G., Phillips S., and Restivo R. J. Chem. Soc., Chem. Commun. (1974) 112
47. Bäckvall J.E. Tetrahedron Lett. 19 (1978) 163
48. Bäckvall J.E. Acc. Chem. Res. 16 (1983) 335
49. For examples, see:
50. Tichenor M.S., Trzupek J.D., Kastrinsky D.B., Shiga F., Hwang I., and Boger D.L. J. Am. Chem. Soc. 128 (2006) 15683
51. Boger D.L., and Garbaccio R.M. J. Org. Chem. 64 (1999) 8350
52. Zhang Q., and Lu X. J. Am. Chem. Soc. 122 (2000) 7604
53. Heck R.F. Org. React. 27 (1982) 345
54. Larhed M., and Hallberg A. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley-Interscience, New York, NY
55. Soderberg B.C. In: Hegedus L.S., Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford pp 259-287
56. For examples, see:
57. Desai L., Malik H.A., and Sanford M.S. Org. Lett. 8 (2006) 1141
58. Yang D. Acc. Chem. Res. 37 (2004) 497
59. Muehlhofer M., Strassner T., and Herrmann W.A. Angew. Chem., Int. Ed. 124 (2002) 3824
60. Reddy B.V.S., Reddy L.F., and Corey E.J. Org. Lett. 8 (2006) 3391
61. Tang S., Peng P., Pi S.F., Liang Y., Wang N.X., and Li J.H. Org. Lett. 10 (2008) 1179
62. Wang G.W., Yuan T.T., and Wu X.L. J. Org. Chem. 73 (2008) 4717
63. The olefin geometry of these side products could not be definitively determined using NOE analysis.
64. Alexanian E.J., Lee C., and Sorensen E.J. J. Am. Chem. Soc. 127 (2005) 7690
65. Li Y., Song D., and Dong V.M. J. Am. Chem. Soc. 130 (2008) 2962
66. Dick A.R., Kampf J., and Sanford M.S. J. Am. Chem. Soc. 127 (2005) 12790
67. Reductive elimination from a similar intermediate has been reported to proceed with inversion, as determined by coupling constant analysis (see Ref. 11b).
68. The olefin geometry of 39c could not be definitively determined in solution via NOE analysis; however, interestingly, the X-ray structure shows a geometry consistent with initial cis-acetoxypalladation of the alkyne. While the literature suggests that trans-acetoxypalladation should predominate under our standard reaction conditions, early studies of alkyne halo- and acetoxypalladation have shown that mixtures of trans and cis products can be formed. For examples, see:
69. Lu X., Zhu G., and Ma S. Tetrahedron Lett. 33 (1992) 7205
70. Zhu G., Ma S., Lu X., and Huang Q. J. Chem. Soc., Chem. Commun. (1995) 271
71. Lambert C., Utimoto K., and Nazaki H. Tetrahedron Lett. 25 (1984) 5323
72. Yanagihara N., Lambert C., Iritani K., Utimoto K., and Nozaki H. J. Am. Chem. Soc. 108 (1986) 2753
73. Bäckvall J.-E., Nilsson Y.I.M., and Gatti R.G.P. Organometallics 14 (1995) 4242 Further investigations are underway to understand the factors controlling cis versus trans acetoxypalladation as well as the effect that this has on the outcome of these cyclopropane-forming transformations
74. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 704193. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
75. Kinetics studies have shown that these reactions are zero order in oxidant. Therefore, the change in rate with electronically differentiated alkenes does not provide information about the cyclopropane-forming step of this reaction.
76. In contrast, significant decomposition of the alkene products (β-H) was observed under these conditions. Many small peaks were observed in the GC and HPLC traces of these reactions after 8 h, suggesting that β-H decomposes to a mixture of unidentified minor products. We believe that this accounts for the poor mass balance in many of these reactions.