Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2

Angewandte Chemie - International Edition

Volumn 55, Issue 16, 2016, Pages 5053-5057

  Moragas, Toni ^a   Gaydou, Morgane ^a   Martin, Ruben ^a,b  

^a BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

C N activation; carboxylation; homogeneous catalysis; nickel; reductive coupling

Indexed keywords

CARBOXYLATION; CATALYSIS; NICKEL;

BENZYLIC; ELECTROPHILES; HOMODIMERIZATION; HOMOGENEOUS CATALYSIS; HYDRIDE ELIMINATION; REDUCTIVE COUPLINGS; STATE-OF-THE-ART TECHNIQUES; USER FRIENDLY;

CARBON DIOXIDE;

EID: 84962556587     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201600697     Document Type: Article

References (95)

1. J. Gu, X. Wang, W. Xue, H. Gong, Org. Chem. Front. 2015, 2, 1411-1421;
2. J. D. Weix, Acc. Chem. Res. 2015, 48, 1767-1775;
3. T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 2014, 20, 8242-8258;
4. C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. Jacobi von Wangelin, Chem. Eur. J. 2014, 20, 6828-6842.
5. S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299-309;
6. "Organonickel Chemistry" Organometallics in Synthesis: Fourth Manual (Eds.:, B. H. Lipshutz,), Wiley, Hoboken, 2013;
7. Metal-Catalyzed Cross-Coupling Reactions (Eds:, F. Diederich, A. Meijere,), Wiley-VCH, Weinheim, 2004.
8. L. Zhang, Z. Hou, Chem. Sci. 2013, 4, 3395-3403;
9. Y. Tsuji, T. Fujihara, Chem. Commun. 2012, 48, 9956-9964;
10. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kuhn, Angew. Chem. Int. Ed. 2011, 50, 8510-8537;
11. Angew. Chem. 2011, 123, 8662-8690;
12. K. Huang, C.-L. Sun, Z.-J. Shi, Chem. Soc. Rev. 2011, 40, 2435-2452;
13. R. Martin, A. W. Kleij, ChemSusChem 2011, 4, 1259-1263;
14. T. Sakakura, J. C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365-2387.
15. K. Osakada, R. Sato, T. Yamamoto, Organometallics 1994, 13, 4645-4647.
16. X. Wang, M. Nakajima, R. Martin, J. Am. Chem. Soc. 2015, 137, 8924-8927;
17. X. Wang, Y. Liu, R. Martin, J. Am. Chem. Soc. 2015, 137, 6476-6479;
18. T. Moragas, J. Cornella, R. Martin, J. Am. Chem. Soc. 2014, 136, 17702-17705;
19. Y. Liu, J. Cornella, R. Martin, J. Am. Chem. Soc. 2014, 136, 11212-11215;
20. A. Correa, T. León, R. Martin, J. Am. Chem. Soc. 2014, 136, 1062-1069;
21. T. León, A. Correa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1221-1224;
22. A. Correa, R. Martin, J. Am. Chem. Soc. 2009, 131, 15974-15975.
23. K. Nogi, T. Fujihara, J. Terao, Y. Tsuji, J. Org. Chem. 2015, 80, 11618-11623;
24. F. Rebih, M. Andreini, A. Moncomble, A. Harrison-Marchand, J. Maddaluno, M. Durandetti, Chem. Eur. J. 2016, 22, 3758-3763;
25. T. Mita, Y. Higuchi, Y. Sato, Chem. Eur. J. 2015, 21, 16391-16394;
26. K. Nogi, T. Fujihara, J. Terao, Y. Tsuji, Chem. Commun. 2014, 50, 13052-13055;
27. H. Tran-Vu, O. Daugulis, ACS Catal. 2013, 3, 2417-2420;
28. T. Fujihara, K. Nogi, T. Xu, J. Terao, Y. Tsuji, J. Am. Chem. Soc. 2012, 134, 9106-9109.
29. For a review, see:, A. Correa, R. Martin, Angew. Chem. Int. Ed. 2009, 48, 6201-6204;
30. Angew. Chem. 2009, 121, 6317-6320.
31. A. Ueno, M. Takimoto, W. W. N. O. M. Nishiura, T. Ikariya, Z. Hou, Chem. Asian J. 2015, 10, 1010-1016;
32. M. Takimoto, Z. Hou, Chem. Eur. J. 2013, 19, 11439-11445;
33. S. Li, B. Miao, W. Yuan, S. Ma, Org. Lett. 2013, 15, 977-979;
34. A. Metzger, S. Bernhardt, G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2010, 49, 4665-4668;
35. Angew. Chem. 2010, 122, 4769-4773;
36. T. Ohishi, M. Nishiura, Z. Hou, Angew. Chem. Int. Ed. 2008, 47, 5792-5795;
37. Angew. Chem. 2008, 120, 5876-5879;
38. J. Takaya, S. Tadami, K. Ukai, N. Iwasawa, Org. Lett. 2008, 10, 2697-2700;
39. C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 7826-7827;
40. K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706-8707.
41. M. D. Greenhalgh, S. P. Thomas, J. Am. Chem. Soc. 2012, 134, 11900-11903;
42. C. M. Williams, J. B. Johnson, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14936-14937;
43. H. Hoberg, Y. Peres, C. Kruger, Y.-H. Tsay, Angew. Chem. Int. Ed. Engl. 1987, 26, 771-773;
44. Angew. Chem. 1987, 99, 799-800.
45. Recently, an elegant solution to prevent homodimerization in primary benzyl alcohol derivatives lacking β-hydrogens has been accomplished by Weix and co-workers using cobalt phthalocyanine. See:, L. K. G. Ackerman, L. L. Anka-Lufford, M. Naodovic, D. J. Weix, Chem. Sci. 2015, 6, 1115-1119.
46. R. N. Icke, B. B. Wisegarver, G. A. Alles, Org. Synth. 1945, 25, 89-91.
47. Q. Wang, Y. Su, H. Huang, Chem. Soc. Rev. 2016, 45, 1257-1272;
48. K. Ouyang, W. Hao, W.-X. Zhang, Z. Xi, Chem. Rev. 2015, 115, 12045-12090.
49. H. Zhang, S. Hagihara, K. Itami, Chem. Eur. J. 2015, 21, 16796-16800;
50. X.-Q. Zhang, Z.-X. Wang, Org. Biomol. Chem. 2014, 12, 1448-1453;
51. P. Maity, D. M. Shacklady-McAtee, G. P. A. Yap, E. R. Sirianni, M. P. Watson, J. Am. Chem. Soc. 2013, 135, 280-285;
52. L.-G. Xie, Z.-X. Wang, Angew. Chem. Int. Ed. 2011, 50, 4901-4904;
53. Angew. Chem. 2011, 123, 5003-5006;
54. S. B. Blakey, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 6046-6047;
55. E. Wenkert, A.-L. Han, C.-J. Jenny, J. Chem. Soc. Chem. Commun. 1988, 975-976.
56. L. Hie, N. F. Fine Nathel, T. K. Shah, E. L. Baker, X. Hong, Y.-F. Yang, P. Liu, K. N. Houk, N. K. Garg, Nature 2015, 524, 79-83;
57. M. Tobisu, K. Nakamura, N. Chatani, J. Am. Chem. Soc. 2014, 136, 5587-5590;
58. T. Koreeda, T. Kochi, F. Kakiuchi, J. Am. Chem. Soc. 2009, 131, 7238-7239;
59. S. Ueno, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 6098-6099.
60. The nature of both the substituents on nitrogen and the counterion of the ammonium salt exerted a profound influence on reactivity. See Ref. [15]. The reduction of the ammonium salt accounts for the mass balance.
61. Lower yields of 2 a (60-73 %) were detected in the presence of 10-20 mol % COD. For examples showing the inhibition by COD, see
62. A. J. Nett, W. Zhao, P. M. Zimmerman, J. Montgomery, J. Am. Chem. Soc. 2015, 137, 7636-7639;
63. J. Cornella, E. Gomez-Bengoa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1997-2009;
64. A. Fürstner, K. Majima, R. Martin, H. Krause, E. Kattnig, R. Goddard, W. Lehmann, J. Am. Chem. Soc. 2008, 130, 1992-2004.
65. T. Fujihara, Y. Horimoto, T. Mizoe, F. B. Sayyed, Y. Tani, J. Terao, S. Sakaki, Y. Tsuji, Org. Lett. 2014, 16, 4960-4963;
66. C. Zhao, X. Jia, X. Wang, H. Gong, J. Am. Chem. Soc. 2014, 136, 17645-17651;
67. F. Wu, W. Lu, Q. Qian, Q. Ren, H. Gong, Org. Lett. 2012, 14, 3044-3047;
68. H. Yin, C. Zhao, H. You, K. Lin, H. Gong, Chem. Commun. 2012, 48, 7034-7036.
69. For an elegant study showing the intriguing impact of different substitution patterns for 1,10-phenanthroline backbones on catalytic performance, see:, C. Cheng, J. F. Hartwig, J. Am. Chem. Soc. 2015, 137, 592-595.
70. S. R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 2005, 44, 7674-7684;
71. Angew. Chem. 2005, 117, 7848-7859;
72. Catalyst Poisoning (Eds.:, L. L. Hegedus, R. W. McCabe,), Marcel-Dekker, New York, 1984;
73. S. G. Murray, F. R. Hartley, Chem. Rev. 1981, 81, 365-414.
74. Low yields of 4 a were found when using a procedure based on L4, suggesting that the success of L6 might be attributed to electronic effects by facilitating oxidative addition. For an analogous observation in other catalytic scenarios, see Ref. [19].
75. P. Novák, R. Martin, Curr. Org. Chem. 2011, 15, 3233-3262;
76. C. C. C. Johansson, T. J. Colacot, Angew. Chem. Int. Ed. 2010, 49, 676-707;
77. Angew. Chem. 2010, 122, 686-718;
78. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146.
79. H. Cong, G. C. Fu, J. Am. Chem. Soc. 2014, 136, 3788-3791;
80. M. R. Harris, M. O. Konev, E. R. Jarvo, J. Am. Chem. Soc. 2014, 136, 7825-7828.
81. D. C. Powers, B. L. Anderson, D. G. Nocera, J. Am. Chem. Soc. 2013, 135, 18876-18883.
82. CCDC 1448910 (5) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
83. CCDC 1448911 (6) contains the supplementary crystallographic data for this paper.
84. C. A. Laskowski, D. J. Bungum, S. M. Baldwin, S. A. Del Ciello, V. M. Iluc, G. L. Hillhouse, J. Am. Chem. Soc. 2013, 135, 18272-18275;
85. J. Breitenfeld, J. Ruiz, M. D. Wodrich, X. Hu, J. Am. Chem. Soc. 2013, 135, 12004-12012;
86. S. Biswas, D. J. Weix, J. Am. Chem. Soc. 2013, 135, 16192-16197.
87. A significant inhibition was detected in the presence of radical scavengers, such as 2,2,6,6-tetramethylpiperidine N-oxide (TEMPO) or galvinoxyl, for either 2 a or 3 a (17-45 % yield).
88. n species. See, for example:, I. M. Yonova, A. G. Johnson, C. A. Osborne, C. E. Moore, N. S. Morrissette, E. R. Jarvo, Angew. Chem. Int. Ed. 2014, 53, 2422-2427;
89. Angew. Chem. 2014, 126, 2454-2459.
90. A. Velian, S. Lin, A. J. M. Miller, M. W. Day, T. Agapie, J. Am. Chem. Soc. 2010, 132, 6296-6297;
91. V. B. Phapale, E. Bunuel, M. García-Iglesias, D. J. Cardenas, Angew. Chem. Int. Ed. 2007, 46, 8790-8795;
92. Angew. Chem. 2007, 119, 8946-8951;
93. G. D. Jones, J. L. Martin, C. McFarland, O. R. Allen, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicic, J. Am. Chem. Soc. 2006, 128, 13175-13183.
94. 2:, F. S. Menges, S. M. Craig, N. Tötsch, A. Bloomfield, S. Ghosh, H.-J. Krüger, M. A. Johnson, Angew. Chem. Int. Ed. 2016, 55, 1282-1285;
95. Angew. Chem. 2016, 128, 1304-1307.