Palladium-Catalyzed C-H Functionalization of Acyldiazomethane and Tandem Cross-Coupling Reactions

Journal of the American Chemical Society

Volumn 137, Issue 13, 2015, Pages 4435-4444

  Ye, Fei ^a   Qu, Shuanglin ^b   Zhou, Lei ^c   Peng, Cheng ^a   Wang, Chengpeng ^a   Cheng, Jiajia ^a   Hossain, Mohammad Lokman ^a   Liu, Yizhou ^a   Zhang, Yan ^a   Wang, Zhi Xiang ^b   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; ORGANIC COMPOUNDS; PALLADIUM; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

C-H FUNCTIONALIZATION; CROSS COUPLING REACTIONS; ETHYL DIAZOACETATE; MIGRATORY INSERTION; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; REACTIVE INTERMEDIATE; REDUCTIVE ELIMINATION;

DENSITY FUNCTIONAL THEORY;

CARBENE; DIAZOACETIC ACID ETHYL ESTER; FUNCTIONAL GROUP; IODIDE; METHANE; PALLADIUM; AZO COMPOUND; CARBON; HYDROGEN;

ARTICLE; ARYLATION; CATALYST; COLUMN CHROMATOGRAPHY; CROSS COUPLING REACTION; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS; THERMODYNAMICS; TRANS ISOMER; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; QUANTUM THEORY;

AZO COMPOUNDS; CARBON; CATALYSIS; HYDROGEN; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PALLADIUM; QUANTUM THEORY; THERMODYNAMICS;

EID: 84926442923     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja513275c     Document Type: Article

References (106)

1. Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797
2. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1901
3. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223
4. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
5. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911
6. Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50
7. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
8. Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2004, 3773
9. Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem. 2005, 3, 4176
10. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
11. Zhou, C.-Y.; Huang, J.-S.; Che, C.-M. Synlett 2010, 2681
12. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
13. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
14. Davies, H. M. L.; Lian, Y. Acc. Chem. Res. 2012, 45, 923
15. Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365
16. Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427
17. Murphy, G. K.; Stewart, C.; West, F. G. Tetrahedron 2013, 69, 2667
18. Peng, C.; Cheng, J.; Wang, J. J. Am. Chem. Soc. 2007, 129, 8708
19. Bablinski, D. J.; Aguilar, H. R.; Still, R.; Frantz, D. E. J. Org. Chem. 2011, 76, 5915
20. Eidamshaus, C.; Hommes, P.; Reissig, H.-U. Synlett 2012, 23, 1670
21. Crabtree, R. H. Chem. Rev. 1985, 85, 245
22. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2004.
23. Dyker, G. Handbook of C-H Transformations. Applications in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2005.
24. Godula, K.; Sames, D. Science 2006, 312, 67
25. Bergman, R. G. Nature 2007, 446, 391
26. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
27. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
28. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
29. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
30. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
31. Ackermann, L. Chem. Rev. 2011, 111, 1315
32. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
33. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
34. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588
35. Maas, G. Angew. Chem., Int. Ed. 2009, 48, 8186
36. Ye, F.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 11625
37. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 1015
38. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
39. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2011, 41, 560
40. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
41. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586
42. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
43. Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219
44. Barluenga, J.; Moriel, P.; Valdés, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 5587
45. Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566
46. Kudirka, R.; Devine, S. K. J.; Adams, C. S.; Van Vranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677
47. Yu, W.-Y.; Tsoi, Y.-T.; Zhou, Z.; Chan, A. S. C. Org. Lett. 2009, 11, 469
48. Barluenga, J.; Escribano, M.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2010, 49, 6856
49. Zhao, X.; Jing, J.; Lu, K.; Zhang, Y.; Wang, J. Chem. Commun. 2010, 1724
50. Zhou, L.; Ye, F.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2010, 132, 13590
51. Barluenga, J.; Quiñones, N.; Cabal, M.-P.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 2350
52. Zhou, L.; Ye, F.; Ma, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 3510
53. Chen, Z.-S.; Duan, X.-H.; Wu, L.-Y.; Ali, S.; Ji, K.-G.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2011, 17, 6918
54. Ojha, D. P.; Prabhu, K. R. J. Org. Chem. 2012, 77, 11027
55. Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565
56. Roche, M.; Hamze, A.; Brion, J.-D.; Alami, M. Org. Lett. 2013, 15, 148
57. Yadav, A. K.; Srivastava, V. P.; Yadav, L. D. S. Chem. Commun. 2013, 49, 2154
58. Yang, K.; Zhang, J.; Li, Y.; Cheng, B.; Zhao, L.; Zhai, H. Org. Lett. 2013, 15, 808
59. Zeng, X.; Cheng, G.; Shen, J.; Cui, X. Org. Lett. 2013, 15, 3022
60. Liu, X.; Ma, X.; Huang, Y.; Gu, Z. Org. Lett. 2013, 15, 4814
61. Barroso, R.; Valencia, R. A.; Cabal, M.-P.; Valdés, C. Org. Lett. 2014, 16, 2264
62. Wang, P.-S.; Lin, H.-C.; Zhou, X.-L.; Gong, L.-Z. Org. Lett. 2014, 16, 3332
63. Zhou, P.-X.; Ye, Y.-Y.; Ma, J.-W.; Zheng, L.; Tang, Q.; Qiu, Y.-F.; Song, B.; Qiu, Z.-H.; Xu, P.-F.; Liang, Y.-M. J. Org. Chem. 2014, 79, 6627
64. Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365
65. Müller, T. J. J. Top. Organomet. Chem. 2006, 19, 149
66. Shindoh, N.; Takemoto, Y.; Takasu, K. Chem.-Eur. J. 2009, 15, 12168
67. Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754
68. Ajamian, A.; Gleason, J. L. Chem. Rev. 2005, 105, 1001
69. Albrecht, Ł.; Jiang, H.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2011, 50, 8492
70. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
71. Vaxelaire, C.; Winter, P.; Christmann, M. Angew. Chem., Int. Ed. 2011, 50, 3605
72. Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162
73. Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 833
74. Johansen, M. B.; Kerr, M. A. Org. Lett. 2010, 12, 4956
75. Cai, Y.; Zhu, S.-F.; Wang, G.-P.; Zhou, Q.-L. Adv. Synth. Catal. 2011, 353, 2939
76. Lee, E. C.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 12066
77. Hou, Z.; Wang, J.; He, P.; Wang, J.; Qin, B.; Liu, X.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2010, 49, 4763
78. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
79. All the structures were optimized and characterized to be energy minima or transition states at M06/BSI level, where BSI denotes a basis set of LANL2DZ for Pd, I, Ag and 6-31G(d) for other atoms. The energies were then improved by M06/BSII//M06/BSI single-point calculations with the solvent effects accounted by SMD solvent model, using toluene as the solvent. BSII denotes a basis set of SDD for Pd, I, Ag and 6-311++G(d,p) for other atoms. The gas-phase M06/BSI harmonic frequencies were used for thermal corrections to free energies at 298.15 K and 1 atm. More details are given in Supporting Information.
80. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
81. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
82. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704
83. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874
84. Suzuki, A. J. Organomet. Chem. 1999, 576, 147
85. Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954
86. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647
87. Ahlquist, M.; Norrby, P. O. Organometallics 2007, 26, 550
88. Lam, K. C.; Marder, T. B.; Lin, Z. Y. Organometallics 2007, 26, 758
89. Surawatanawong, P.; Fan, Y.; Hall, M. B. J. Organomet. Chem. 2008, 693, 1552
90. Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P. O. Organometallics 2006, 25, 2066
91. Wiberg, K. B. Tetrahedron 1968, 24, 1083
92. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
93. Taubmann, C.; Öfele, K.; Herdtweck, E.; Herrmann, W. A. Organometallics 2009, 28, 4254
94. Taubmann, C.; Tosh, E.; Öfele, K.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2008, 693, 2231
95. Herrmann, W. A.; Öfele, K.; Taubmann, C.; Herdtweck, E.; Hoffmann, S. D. J. Organomet. Chem. 2007, 692, 3846
96. Schneider, S. K.; Roembke, P.; Julius, G. R.; Raubenheimer, H. G.; Herrmanna, W. A. Adv. Synth. Catal. 2006, 348, 1862
97. Schuster, O.; Raubenheimer, H. G. Inorg. Chem. 2006, 45, 7997
98. Oulié, P.; Nebra, N.; Saffon, N.; Maron, L.; Martin-Vaca, B.; Bourissou, D. J. Am. Chem. Soc. 2009, 131, 3493
99. Weng, W.; Chen, C.-H.; Foxman, B. M.; Ozerov, O. V. Organometallics 2007, 26, 3315
100. Stander-Grobler, E.; Schuster, O.; Heydenrych, G.; Cronje, S.; Tosh, E.; Albrecht, M.; Frenking, G.; Raubenheimer, H. G. Organometallics 2010, 29, 5821
101. Kessler, F.; Szesni, N.; Põhako, K.; Weibert, B.; Fischer, H. Organometallics 2009, 28, 348
102. Vignolle, J.; Gornitzka, H.; Donnadieu, B.; Bourissou, D.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 2271
103. Xia, Y.; Qu, S.; Xiao, Q.; Wang, Z.-X.; Qu, P.; Chen, L.; Liu, Z.; Tian, L.; Huang, Z.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 13502
104. Negishi, E.-i.; de Meijere, A. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
105. Muzart, J. J. Mol. Catal. A: Chem. 2009, 308, 15
106. Kuehne, M. E.; Hall, T. C. J. Org. Chem. 1976, 41, 2742