A new approach to carbon-carbon bond formation: development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes

Tetrahedron

Volumn 65, Issue 26, 2009, Pages 5074-5083

  Gligorich, Keith M ^a   Iwai, Yasumasa ^b   Cummings, Sarah A ^c   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

^b KYORIN PHARMACEUTICAL CO LTD   (Japan)

^c UNIVERSITY OF NEVADA   (United States)

Author keywords

Catalysis; Cross coupling; Mechanism; Molecular Oxygen; Palladium

Indexed keywords

CARBON; ORGANOMETALLIC COMPOUND; PALLADIUM; STYRENE DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 65749088277     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.096     Document Type: Article

References (79)

1. Beller M., Seayad J., Tillack A., and Jiao H. Angew. Chem., Int. Ed. 43 (2004) 3368-3398
2. Tsuji J. Palladium Reagents and Catalysts (2004), John Wiley & Sons, Hoboken, NJ
3. Stahl S.S. Angew. Chem., Int. Ed. 43 (2004) 3400-3420
4. Cornell C.N., and Sigman M.S. Inorg. Chem. 46 (2007) 1903-1909
5. Cornell C.N., and Sigman M.S. J. Am. Chem. Soc. 127 (2005) 2796-2797
6. Cornell C.N., and Sigman M.S. Org. Lett. 8 (2006) 4117-4120
7. Gligorich K.M., Schultz M.J., and Sigman M.S. J. Am. Chem. Soc. 128 (2006) 2794-2795
8. Zhang Y., and Sigman M.S. Org. Lett. 8 (2006) 5557-5560
9. II-catalyzed coupled alcohol oxidation/alkene hydrogenation, see:. Tsuchiya Y., Hamashima Y., and Sodeoka M. Org. Lett. 8 (2006) 4851-4854
10. For examples of metal catalyzed alkene hydroalkoxylation reactions, see:
11. Qian H., Han X., and Widenhoefer R.A. J. Am. Chem. Soc. 126 (2004) 9536-9537
12. Yang C.-G., Reich N.W., Shi Z., and He C. Org. Lett. 7 (2005) 4553-4556
13. Coulombel L., Favier I., and Dunach E. Chem. Commun. (2005) 2286-2288
14. Yang C.-G., and He C. J. Am. Chem. Soc. 127 (2005) 6966-6967
15. For an example of a Pd(0)-catalyzed hydroalkoxylation, see:. Matsukawa Y., Mizukado J., Quan H., Tamura M., and Sekiya A. Angew. Chem., Int. Ed. 44 (2005) 1128-1130
16. For a review of quinone methides in synthesis, see:. Van De Water R.W., and Pettus T.R.R. Tetrahedron 58 (2002) 5367-5405
17. For the use of stoichiometric Pd(II)/Cu(II) to generate a quinone methide in the elegant synthesis of carpanone, see:. Chapman O.L., Engel M.R., Springer J.P., and Clardy J.C. J. Am. Chem. Soc. 93 (1971) 6696-6698
18. Stahl S.S. Science 309 (2005) 1824-1826
19. Gligorich K.M., and Sigman M.S. Angew. Chem., Int. Ed. 45 (2006) 6612-6615
20. Gligorich K.M., Cummings S.A., and Sigman M.S. J. Am. Chem. Soc. 129 (2007) 14193-14195
21. Netherton M.R., and Fu G.C. Palladium-Catalyzed Cross-Coupling Reactions of Unactivated Alkyl Electrophiles with Organometallic Compounds. Topics in Organometallic Chemistry Vol. 14 (2005), Springer, Berlin pp 85-108
22. For selected examples of the oxidative Heck reaction, see:
23. Hirabayashi K., Ando J.-I., Nishihara Y., Mori A., and Hiyama T. Synlett (1999) 99-101
24. Andappan M.M.S., Nilsson P., and Larhed M. Chem. Commun. (2004) 218-219
25. Delcamp J.H., Brucks A.P., and White M.C. J. Am. Chem. Soc. 130 (2008) 11270-11271 For a mechanistic study of the oxidative Heck reaction, see:
26. Enquist P.A., Nilsson P., Sjoberg P., and Larhed M. J. Org. Chem. 71 (2006) 8779-8786
27. II-catalyzed homocoupling of organometallic reagents, see:
28. Alcaraz L., and Taylor R.J.K. Synlett (1997) 791-792
29. Smith K.A., Campi E.M., Jackson W.R., Marcuccio S., Naeslund C.G.M., and Deacon G.B. Synlett (1997) 131-132
30. II-catalyzed homocoupling of organoboronic acids, see:
31. Adamo C., Amatore C., Ciofini I., Jutand A., and Lakmini H. J. Am. Chem. Soc. 128 (2006) 6829-6836
32. Mueller J.A., and Sigman M.S. J. Am. Chem. Soc. 125 (2003) 7005-7013
33. Mueller J.A., Goller C.P., and Sigman M.S. J. Am. Chem. Soc. 126 (2004) 9724-9734
34. Mueller J.A., Cowell A., Chandler B.D., and Sigman M.S. J. Am. Chem. Soc. 127 (2005) 14817-14824
35. Sigman M.S., and Jensen D.R. Acc. Chem. Res. 39 (2006) 221-229
36. Balija A.M., Stowers K.J., Schultz M.J., and Sigman M.S. Org. Lett. 8 (2006) 1121-1124
37. Podhajsky S.M., and Sigman M.S. Organometallics 26 (2007) 5680-5686
38. Nishimura T., Kakiuchi N., Onoue T., Ohe K., and Uemura S. J. Chem. Soc., Perkin Trans. 1 (2000) 1915-1918
39. Sen A., and Lai T.W. Inorg. Chem. 23 (1984) 3257-3258
40. For a review of the Stille reaction, see:. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 4704-4734
41. Shirakawa E., Nakao Y., Murota Y., and Hiyama T. J. Organomet. Chem. 670 (2003) 132-136
42. For a Rh-catalyzed hydroarylation reaction of vinyl pyridines, see:. Lautens M., Roy A., Fukuoka K., Fagnou K., and Martin-Matute B. J. Am. Chem. Soc. 123 (2001) 5358-5359
43. II-catalyzed hydroarylation reaction of Michael acceptors, see:. Ohe T., Wakita T., Motofusa S.-i., Cho C.S., Ohe K., and Uemura S. Bull. Chem. Soc. Jpn. 73 (2000) 2149-2155
44. Oda H., Morishita M., Fugami K., Sano H., and Kosugi M. Chem. Lett. (1996) 811-812
45. Fugami K., Hagiwara S., Oda H., and Kosugi M. Synlett (1998) 477-478
46. Conley N.R., Labios L.A., Pearson D.M., McCrory C.C.L., and Waymouth R.M. Organometallics 26 (2007) 5447-5453
47. Konnick M.M., and Stahl S.S. J. Am. Chem. Soc. 130 (2008) 5753-5762
48. Boczon W., Pieczonka G., and Wiewiorowski M. Tetrahedron 33 (1977) 2565-2570
49. Larson E.J., and Pecoraro V.L. J. Am. Chem. Soc. 113 (1991) 7809-7810
50. Steinhoff B.A., and Stahl S.S. J. Am. Chem. Soc. 128 (2006) 4348-4355
51. Fischer K., and Wilken M. J. Chem. Thermodyn. 33 (2001) 1285-1308
52. Iwasawa T., Tokunaga M., Obora Y., and Tsuji Y. J. Am. Chem. Soc. 126 (2004) 6554-6555
53. Barda D.A., Wang Z.-Q., Britton T.C., Henry S.S., Jagdmann G.E., Coleman D.S., Johnson M.P., Andis S.L., and Schoepp D.D. Bioorg. Med. Chem. Lett. 14 (2004) 3099-3102
54. Moriconi A., Cesta M.C., Cervellera M.N., Aramini A., Coniglio S., Colagioia S., Beccari A.R., Bizzarri C., Cavicchia M.R., Locati M., Galliera E., Di Benedetto P., Vigilante P., Bertini R., and Allegretti M. J. Med. Chem. 50 (2007) 3984-4002
55. Liang H., Wu X., Yalowich J.C., and Hasinoff B.B. Mol. Pharmacol. 73 (2008) 686-696
56. For selected examples of alkene hydroarylation reactions, see:
57. Youn So W., Pastine Stefan J., and Sames D. Org. Lett. 6 (2004) 581-584
58. Nevado C., and Echavarren A.M. Synthesis (2005) 167-182
59. Anderson L.L., Arnold J., and Bergman R.G. J. Am. Chem. Soc. 127 (2005) 14542-14543
60. Han X., and Widenhoefer R.A. Org. Lett. 8 (2006) 3801-3804
61. Lapis A.A.M., Da Silveira Neto B.A., Scholten J.D., Nachtigall F.M., Eberlin M.N., and Dupont J. Tetrahedron Lett. 47 (2006) 6775-6779
62. Rueping M., Nachtsheim B.J., and Scheidt T. Org. Lett. 8 (2006) 3717-3719
63. Sun G., Sun H., Wang Z., and Zhou M.M. Synlett (2008) 1096-1100
64. For a review of the hydrovinylation reaction, see:. RajanBabu T.V. Chem. Rev. 103 (2003) 2845-2860
65. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
66. Kotha S., Lahiri K., and Kashinath D. Tetrahedron 58 (2002) 9633-9695
67. Chemler S.R., Trauner D., and Danishefsky S.J. Angew. Chem., Int. Ed. 40 (2001) 4544-4568
68. Miyaura N. J. Organomet. Chem. 653 (2002) 54-57
69. Iwai Y., Gligorich K.M., and Sigman M.S. Angew. Chem., Int. Ed. 47 (2008) 3219-3222
70. Johns A.M., Utsunomiya M., Incarvito C.D., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 1828-1839
71. Grushin V.V. Chem. Rev. 96 (1996) 2011-2033
72. Konnick M.M., Gandhi B.A., Guzei I.A., and Stahl S.S. Angew. Chem., Int. Ed. 45 (2006) 2790-2793
73. Johns A.M., Tye J.W., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 16010-16011
74. Mabbott D.J., and Maitlis P.M. J. Chem. Soc., Dalton Trans. (1976) 2156-2160
75. Hills I.D., and Fu G.C. J. Am. Chem. Soc. 126 (2004) 13178-13179
76. O'Brien C.J., Kantchev E.A.B., Valente C., Hadei N., Chass G.A., Lough A., Hopkinson A.C., and Organ M.G. Chem.-Eur. J. 12 (2006) 4743-4748
77. Mandal S.K., and Sigman M.S. J. Org. Chem. 68 (2003) 7535-7537
78. Mueller J.A., Jensen D.R., and Sigman M.S. J. Am. Chem. Soc. 124 (2002) 8202-8203
79. Renaud P., Lacote E., and Quaranta L. Tetrahedron Lett. 39 (1998) 2123-2126