Palladium-catalyzed oxidative arylhalogenation of alkenes: Synthetic scope and mechanistic insights

Journal of the American Chemical Society

Volumn 132, Issue 24, 2010, Pages 8419-8427

  Kalyani, Dipannita ^a   Satterfield, Andrew D ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON-HALOGEN BOND; CATALYZED REACTIONS; GOOD YIELD; HYDRIDE ELIMINATION; OXIDATIVE FUNCTIONALIZATION; REACTION CONDITIONS; RELATIVE RATES;

OLEFINS; ORGANOMETALLICS; REACTION INTERMEDIATES; STEREOSELECTIVITY;

PALLADIUM;

ALKENE DERIVATIVE; ALKYL GROUP; BENZYL DERIVATIVE; BROMINE; CARBON; CHLORINE; PALLADIUM;

ARTICLE; ARYLHALOGENATION; BROMINATION; CATALYSIS; CHEMICAL BOND; CHLORINATION; HALOGENATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; HALOGENATION; NAPHTHALENES; OXIDATION-REDUCTION; PALLADIUM; SOLVENTS; STEREOISOMERISM; STYRENE; SUBSTRATE SPECIFICITY;

EID: 77953639983     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101851v     Document Type: Article

References (136)

1. Mizoroki, T., Mori, K., and Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581
2. Heck, R. F. and Nolley, J. P. J. Org. Chem. 1972, 37, 2320
3. The Mizoroki-Heck Reaction; Oestreich, M., Ed.; John Wiley & Sons Ltd.: Chichester, U.K., 2009.
4. Cabri, W. and Candiani, I. Acc. Chem. Res. 1995, 28, 2
5. Beletskaya, I. P. and Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
6. Link, J. T. The Intramolecular Heck Reaction. In Organic Reactions; Overman, L. E., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2002; Vol. 60.
7. de Meijere, A. and Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379
8. Brase, S. and de Meijere, A. Cross-Coupling of Organyl Halides with Alkenes: the Heck Reaction. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A. and Diederich, F., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2004.
9. Dounay, A. B. and Overman, L. E. Chem. Rev. 2003, 103, 2945
10. Majumdar, K. C., Ansary, I., Sinha, B., and Chattopadhyay, B. Synthesis 2009, 3593
11. For examples, see
12. Beletskaya, I. P. and Cheprakov, A. V. Focus on Catalyst Development and Ligand Design. In The Mizoroki-Heck Reaction; Oestreich, M., Ed.; Wiley: Chichester, U.K., 2009.
13. Yoo, K. S., ONeill, J., Sakaguchi, S., Giles, R., Lee, J. H., and Jung, K. W. J. Org. Chem. 2010, 75, 95
14. Lamblin, M., Nassar-Hardy, L., Hierso, J.-C., Fouquet, E., and Felpin, F.-X. Adv. Synth. Catal. 2010, 352, 33
15. For examples, see
16. Amatore, C. and Jutand, A. J. Organomet. Chem. 1999, 576, 254
17. Knowles, J. P. and Whiting, A. Org. Biomol. Chem. 2007, 5, 31
18. Carrow, B. P. and Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 79
19. For examples of CO insertion, see
20. Sugihara, T., Coperet, C., Owczarczyk, Z., Harring, L. S., and Negishi, E.-i. J. Am. Chem. Soc. 1994, 116, 7923
21. Artman, G. D., III and Weinreb, S. M. Org. Lett. 2003, 5, 1523
22. For examples of alkyne and alkene instertion, see: Schweizer, S., Song, Z.-Z., Meyer, F. E., Parsons, P. J., and de Meijere, A. Angew. Chem., Int. Ed. 1999, 38, 1452
23. Tietze, L. F., Kahle, K., and Raschke, T. Chem. - Eur. J. 2002, 8, 401
24. For complementary routes to the 1,2-arylfunctionalization of alkenes, see
25. Wolfe, J. P. Synlett 2008, 2913
26. Chemler, S. R. and Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153
27. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5538
28. For related Pd-catalyzed 1,1-diarylation reaction of terminal alkenes, see:
29. Urkalan, K. B. and Sigman, M. S. Angew. Chem., Int. Ed. 2009, 48, 3146
30. Tamaru, Y., Hojo, M., Higashimura, H., and Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1986, 25, 735
31. Tamaru, Y., Hojo, M., Kawamura, S., and Yoshida, Z. J. Org. Chem. 1986, 51, 4089
32. For a related Pd-catalyzed 1,1-acetoxyarylation of α,β- unsaturated olefins, see
33. Rodriguez, A. and Moran, W. J. Eur. J. Org. Chem. 2009, 1313
34. For synthesis of heterocycles via 1,1-arylfunctionalization reactions, see ref 9.
35. Parrish, J. P., Jung, Y. C., Shin, S. I., and Jung, K. W. J. Org. Chem. 2002, 67, 7127
36. For a review on ligand directed C-H functionalization, see
37. Lyons, T. W. and Sanford, M. S. Chem. Rev. 2010, 110, 1147
38. Giri, R., Chen, X., and Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112
39. Kalyani, D., Dick, A. R., Anani, W. Q., and Sanford, M. S. Tetrahedron 2006, 62, 11483
40. Giri, R., Wasa, M., Breazzano, S. P., and Yu, J.-Q. Org. Lett. 2006, 8, 5685
41. Hull, K. L., Anani, W. Q., and Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134
42. Thu, H.-Y., Yu, W.-Y., and Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048
43. Dick, A. R., Hull, K. L., and Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
44. Giri, R., Liang, J., Lei, J. Q., Li, J. J., Wang, D. H., Chen, X., Naggar, I. C., Guo, C., Foxman, B. M., and Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 7420
45. Desai, L. V., Malik, H. A., and Sanford, M. S. Org. Lett. 2006, 8, 1141
46. Desai, L. V., Hull, K. L., and Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542
47. Reddy, B. V. S., Reddy, L. R., and Corey, E. J. Org. Lett. 2006, 8, 3391
48. Wang, D. H., Hao, X. S., Wu, D. F., and Yu, J. Q. Org. Lett. 2006, 8, 3387
49. Neufeldt, S. R. and Sanford, M. S. Org. Lett. 2010, 12, 532
50. Zaitsev, V. G., Shabashov, D., and Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
51. Reference 16e.
52. Giri, R., Maugel, N., Li, J. J., Wang, D. H., Breazzano, S. P., Saunders, L. B., and Yu, J. Q. J. Am. Chem. Soc. 2007, 129, 3510
53. Wasa, M., Engle, K. M., and Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 9886
54. Deprez, N. R. and Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234
55. Shabashov, D. and Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
56. For examples, see
57. Helaja, J. and Gottlich, R. Chem. Commun. 2002, 720
58. Lei, A., Lu, X., and Liu, G. Tetrahedron Lett. 2004, 45, 1785
59. Manzoni, M. R., Zabawa, T. P., Kasi, D., and Chemler, S. R. Organometallics 2004, 23, 5618
60. Michael, F. E., Sibbald, P. A., and Cochran, B. M. Org. Lett. 2008, 10, 793
61. Wu, T., Yin, G., and Liu, G. J. Am. Chem. Soc. 2009, 131, 16354
62. Christie, S. D. R., Warrington, A. D., and Lunniss, C. J. Synthesis 2009, 148
63. Doroski, T. A., Cox, M. R., and Morgan, J. B. Tetrahedron Lett. 2009, 50, 5162
64. For examples, see
65. El-Qisairi, A., Hamed, O., and Henry, P. M. J. Org. Chem. 1998, 63, 2790 and references therein
66. Hamed, O. and Henry, P. M. Organometallics 1998, 17, 5184
67. El-Qisairi, A. K., Qaseer, H. A., and Henry, P. M. J. Organomet. Chem. 2002, 656, 168
68. El-Qisairi, A. K., Qaseer, H. A., Katsigras, G., Lorenzi, P., Trivedi, U., Tracz, S., Hartman, A., Miller, J. A., and Henry, P. M. Org. Lett. 2003, 5, 439
69. For examples, see
70. Streuff, J., Hovelmann, C. H., Nieger, M., and Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586
71. Muñiz, K. J. Am. Chem. Soc. 2007, 129, 14542
72. Muñiz, K., Hovelmann, C. H., and Streuff, J. J. Am. Chem. Soc. 2008, 130, 763
73. Muñiz, K., Streuff, J., Chavez, P., and Hovelmann, C. H. Chem. Asian J. 2008, 3, 1248
74. Sibbald, P. A. and Michael, F. E. Org. Lett. 2009, 11, 1147
75. Qiu, S., Xu, T., Zhou, J., Guo, Y., and Liu, G. J. Am. Chem. Soc. 2010, 132, 2856
76. For examples, see
77. Alexanian, E. J., Lee, C., and Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690
78. Liu, G. and Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179
79. Desai, L. V. and Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737
80. Li, Y., Song, D., and Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962
81. Wang, A., Jiang, H., and Chen, H. J. Am. Chem. Soc. 2009, 131, 3846
82. Wang, W., Wang, F., and Shi, M. Organometallics 2010, 29, 928
83. Sibbald, P. A., Rosewall, C. F., Swartz, R. D., and Michael, F. E. J. Am. Chem. Soc. 2009, 131, 15945
84. For a preliminary account of this work, see
85. Kalyani, D. and Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 2150
86. 3 was chosen as the arylating reagent because it undergoes facile transmetallation with palladium(II) under mild conditions in the absence of strong bases or other additives.
87. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508
88. The 1,1-arylchlorination products typically underwent some decomposition during isolation/chromatographic purification (as reflected in the discrepancy between the isolated yield and the yield determined from analysis of the crude reaction mixtures).
89. 2 and a bromide source.
90. Macdonald, T. L. and Narasimhan, N. J. Org. Chem. 1985, 50, 5000
91. Stang, P. J. and Zhdankin, V. V. Chem. Rev. 1996, 96, 1123
92. Braddock, D. C., Cansell, G., and Hermitage, S. A. Synlett. 2004, 461
93. Karade, N. N., Shirodkar, S. G., Dhoot, B. M., and Waghmare, P. B. J. Chem. Res. 2005, 274
94. 2 did not produce appreciable yields of 1,2- or 1,1-aryliodinated products under any conditions examined.
95. 2 for arylbromination.
96. The 1,2- and 1,1-arylbromination products typically underwent some decomposition during isolation/chromatographic purification (as reflected in the discrepancy between the isolated yield and the yield determined from analysis of the crude reaction mixtures).
97. For analogous reactions between substituted stannanes and vinylnaphthalene/styrene, see Table S5.
98. 1H NMR spectroscopy (based on chemical shift and coupling constant analysis) by analogy to several related products that were characterized by X-ray crystallography. See Supporting Information for complete details.
99. 2/THF because this reaction was extremely poor yielding under these conditions.
100. Wax, M. J. and Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 7028
101. II(THF) complexes, see
102. Uson, R., Fornies, J., Tomas, M., and Menjon, B. Organometallics 1985, 4, 1912
103. Sperrle, M., Gramlich, V., and Consiglio, G. Organometallics 1996, 15, 5196
104. Yagyu, T., Hamada, M., Osakada, K., and Yamamoto, T. Organometallics 2001, 20, 1087
105. Clegg, W., Eastham, G. R., Elsegood, M. R. J., Heaton, B. T., Iggo, J. A., Tooze, R. P., Whyman, R., and Zacchini, S. Organometallics 2002, 21, 1832
106. Kim, Y. and Verkade, J. G. J. Organomet. Chem. 2003, 669, 32
107. II(THF) complexes, see
108. Breeze, S. R. and Wang, S. Inorg. Chem. 1993, 32, 5981
109. Amelchenkova, E. V., Denisova, T. O., and Nefedov, S. E. Russ. J. Inorg. Chem. 2006, 51, 1218
110. Becker, Y. and Stille, J. K. J. Am. Chem. Soc. 1978, 100, 845
111. Johns, A. M., Utsunomiya, M., Incarvito, C. D., and Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828
112. Johns, A. M., Tye, J. W., and Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 16010
113. Reference 8.
114. Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707
115. 2, see
116. Lagunas, M.-C., Gossage, R. A., Spek, A. L., and van Koten, G. Organometallics 1998, 17, 731
117. Whitfield, S. R. and Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142
118. 2, see
119. Powers, D. C. and Ritter, T. Nat. Chem. 2009, 1, 302
120. - oxidants, see
121. Lanci, M. P., Remy, M. S., Kaminsky, W., Mayer, J. M., and Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 15618
122. For examples of oxidatively induced carbon-heteroatom bond-forming reactions at Pd with retention of stereochemistry, see ref 21c and
123. Coulson, D. R. J. Am. Chem. Soc. 1969, 91, 200
124. Backvall, J. E. and Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393
125. Zhu, G., Ma, S., Lu, X., and Huang, Q. J. Chem. Soc., Chem. Commun. 1995, 271
126. Zhu, G. and Lu, X. J. Organomet. Chem. 1996, 508, 83
127. Yin, G. and Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442
128. For examples of oxidatively induced carbon-heteroatom bond-forming reactions at Pd with inversion of stereochemistry, see refs 20c, 21b, and
129. Backvall, J. E. Tetrahedron Lett. 1977, 467
130. Backvall, J. E. Tetrahedron Lett. 1978, 163
131. Backvall, J. E. and Bjorkman, E. E. J. Org. Chem. 1980, 45, 2893
132. Tong, X., Beller, M., and Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906
133. Lyons, T. W. and Sanford, M. S. Tetrahedron 2009, 65, 3211
134. For an example of different stereochemical outcomes as a function of reaction conditions, see
135. Wong, P. K. and Stille, J. K. J. Organomet. Chem. 1974, 70, 121
136. See Supporting Information (Table S3) for details.