Ni-catalyzed reductive coupling of alkyl acids with unactivated tertiary alkyl and glycosyl halides

Journal of the American Chemical Society

Volumn 136, Issue 50, 2014, Pages 17645-17651

  Zhao, Chenglong ^a   Jia, Xiao ^a   Wang, Xuan ^a   Gong, Hegui ^a  

^a SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; KETONES; MECHANISMS;

ALKYL BROMIDES; ALKYL HALIDES; GLYCOSYL; MECHANISTIC STUDIES; MULTI-STEP; RADICAL CHAIN MECHANISMS; REDUCTIVE COUPLINGS; SELECTIVE SYNTHESIS;

NICKEL;

ACID; ALKYL ACID; GLYCOSYL HALIDE; HALIDE; NICKEL COMPLEX; RADICAL; TERTIARY ALKYL GROUP; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ARYLATION; CATALYST; CONJUGATE; CONTROLLED STUDY; DECOMPOSITION; MASS FRAGMENTOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 84919393313     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja510653n     Document Type: Article

References (105)

1. Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086
2. Ren, P.; Stern, L. A.; Hu, X. L. Angew. Chem., Int. Ed. 2012, 51, 9110
3. Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen, H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124
4. Iwasaki, T.; Takagawa, H.; Singh, S. P.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2013, 135, 9604
5. Lohre, C.; Dröge, T.; Wang, C.; Glorius, F. Chem.-Eur. J. 2011, 17, 6052
6. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478
7. Ghorai, S. K.; Jin, M.; Hatakeyama, T.; Nakamura, M. Org. Lett. 2012, 14, 1066
8. Someya, H.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 969
9. Mitamura, Y.; Asada, Y.; Murakami, K.; Someya, H.; Yorimitsu, H.; Oshima, K. Chem.-Asian J. 2010, 5, 1487
10. Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137
11. Coupling of tert- alkyl halides with Ar-9BBN: Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 624
12. Smith, S. C.; Fu, G. C. Angew. Chem., Int. Ed. 2008, 47, 9334
13. Han, C.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 7532
14. Thaler, T.; Haag, B.; Gavryushin, A.; Schober, K.; Hartmann, E.; Gschwind, R. M.; Zipse, H.; Mayer, P.; Knochel, P. Nat. Chem. 2010, 2, 125
15. Joshi-Pangu, A.; Ganesh, M.; Biscoe, M. R. Org. Lett. 2011, 13, 1218
16. Li, L.; Wang, C.-Y.; Huang, R.; Biscoe, M. R. Nat. Chem. 2013, 5, 607
17. Liu, Z.; Dong, N.; Xu, M.; Sun, Z.; Tu, T. J. Org. Chem. 2013, 78, 7436
18. For a review on alkyl-organometallics, see: Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
19. Sämann, C.; Dhayalan, V.; Schreiner, P. R.; Knochel, P. Org. Lett. 2014, 16, 2418
20. Johnson, J. B.; Rovis, T. Acc. Chem. Res. 2008, 41, 327
21. Dieter, R. K. Tetrahedron 1999, 55, 4177
22. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1987, 26, 1157
23. Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1700
24. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557
25. Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554
26. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
27. Coia, N.; Mokhtari, N.; Vasse, J.-L.; Szymoniak, J. Org. Lett. 2011, 13, 6292
28. Johnson, J. B.; Bercot, E. A.; Rowley, J. M.; Coates, G. W.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 2718
29. Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 174
30. Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 247
31. Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964
32. Johnson, J. B.; Yu, R. T.; Fink, P.; Bercot, E. A.; Rovis, T. Org. Lett. 2006, 8, 4307
33. Kozuch, S.; Lee, S. E.; Shaik, S. Organometallics. 2009, 28, 1303
34. Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1991, 64, 1999
35. Lee, S. W.; Lee, K.; Seomoon, D.; Kim, S.; Kim, H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Lee, P. H. J. Org. Chem. 2004, 69, 4852
36. Gøgsig, T. M.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. Angew. Chem., Int. Ed. 2012, 51, 798
37. Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726
38. Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656
39. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674
40. Hu, X. Chem. Sci. 2011, 2, 1867
41. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726
42. Devasagayaraj, A.; Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1995, 34, 2723
43. Liu, Y.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 11212
44. Knappke, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; von Wangelin, A. J. Chem.-Eur. J. 2014, 20, 6828
45. Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793
46. Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242
47. Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442
48. Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476
49. Amatore, C.; Jutand, A.; Périchon, J.; Rollin, Y. Monatsh. Chem. 2000, 131, 1293
50. d'Incan, E.; Sibille, S.; Périchon, J.; Moingeon, M.-O.; Chaussard, J. Tetrahedron Lett. 1986, 27, 4175
51. Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 10, 531
52. Yin, H.; Zhao, C.; You, H.; Lin, Q.; Gong, H. Chem. Commun. 2012, 48, 7034
53. Wu, F.; Lu, W.; Qian, Q.; Ren, Q.; Gong, H. Org. Lett. 2012, 14, 3044
54. Lu, W.; Liang, Z.; Zhang, Y.; Wu, F.; Qian, Q.; Gong, H. Synthesis 2013, 45, 2234
55. Bililign, T.; Griffith, B. R.; Thorson, J. S. Nat. Prod. Rep. 2005, 22, 742
56. Hultin, P. G. Curr. Top. Med. Chem. 2005, 5, 1299
57. Zou, W. Curr. Top. Med. Chem. 2005, 5, 1363
58. Compain, P.; Martin, O. R. Bioorg. Med. Chem. 2001, 9, 3077
59. Nicotra, F. Top. Curr. Chem. 1997, 187, 55
60. Wu, Q.; Cho, J.-G.; Lee, D.-S.; Lee, D.-Y.; Song, N.-Y.; Kim, Y.-C.; Lee, K.-T.; Chung, H.-G.; Choi, M.-S.; Jeong, T.-S.; Ahn, E.-M.; Kim, G.-S.; Baek, N.-I. Carbohydr. Res. 2013, 372, 9
61. Disadee, W.; Mahidol, C.; Sahakitpichan, P.; Sitthimonchai, S.; Ruchirawat, S.; Kanchanapoom, T. Phytochemistry 2012, 74, 115
62. Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908
63. Gong, H.; Gagné, M. R. J. Am. Chem. Soc. 2008, 130, 12177
64. Gong, H.; Andrews, R. S.; Zuccarello, J. L.; Lee, S. J.; Gagné, M. R. Org. Lett. 2009, 11, 879
65. Recent α-selective C -glycoside synthesis, Co-catalyzed: Nicolas, L.; Angibaud, P.; Stansfield, I.; Bonnet, P.; Meerpoel, L.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2012, 51, 11101
66. 2Mg to glucosyl bromide: Lemaire, S.; Houpis, I. N.; Xiao, T.; Li, J.; Digard, E.; Gozlan, C.; Liu, R.; Gavryushin, A.; Diène, C.; Wang, Y.; Farina, V.; Knochel, P. Org. Lett. 2012, 14, 1480
67. Somsak, L. Chem. Rev. 2001, 101, 81
68. Deshong, P.; Slough, G. A.; Elango, V.; Trainor, G. L. J. Am. Chem. Soc. 1985, 107, 7788
69. Munro-Leighton, C.; Adduci, L. L.; Becker, J. J.; Gagné, M. R. Organometallics 2011, 30, 2646
70. Vasella, A.; Wenger, W.; Rajamannar, T. Chem. Commun. 1999, 2215
71. Pedretti, V.; Veyrières, A.; Sinaÿ, P. Tetrahedron 1990, 46, 77
72. Obora, Y.; Ogawa, Y.; Imai, Y.; Kawamura, T.; Tsuji, Y. J. Am. Chem. Soc. 2001, 123, 10489
73. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094
74. Pd-catalyzed coupling of sugar-Sn with PhCOCl: Belosludtsev, Y. Y.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1995, 36, 5881
75. Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2005, 70, 9257
76. Knapp, S.; Shieh, W.-C.; Jaramillo, C.; Trilles, R. V.; Nandan, S. R. J. Org. Chem. 1994, 59, 946
77. Wolfgang Weiser, W.; Lehmann, J.; Brewer, C. F.; Hehre, E. J. Carbohydr. Res. 1988, 183, 287
78. álvarez-Dorta, D.; León, E. I.; Kennedy, A. R.; Riesco-Fagundo, C.; Suárez, E. Angew. Chem., Int. Ed. 2008, 47, 8917
79. Geng, Y.; Kumar, A.; Faidallah, H. M.; Albar, H. A.; Mhkalid, I. A.; Schmidt, R. R. Bioorg. Med. Chem. 2013, 21, 4793
80. Jensen, C. M.; Lindsay, K. B.; Taaning, R. H.; Karaffa, J.; Mette Hansen, A.; Skrydstrup, T. J. Am. Chem. Soc. 2005, 127, 6544
81. Wong, C.-H.; Moris-Varas, F.; Hung, S.-C.; Marron, T.-G.; Lin, C.-C.; Gong, K. W.; Weitz-Schmidt, G. J. Am. Chem. Soc. 1997, 119, 8152
82. Peng, Y.; Luo, L.; Yan, C.-S.; Zhang, J.-J.; Wang, Y.-W. J. Org. Chem. 2013, 78, 10960
83. Wada, M.; Murata, T.; Oikawa, H.; Oguri, H. Org. Biomol. Chem. 2014, 12, 298
84. Shukla, P.; Hsu, Y.-C.; Cheng, C.-H. J. Org. Chem. 2006, 71, 655
85. Keh, C. C. K.; Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 4062
86. 2: Bartoli, G.; Bosco, M. Synthesis 2007, 22, 3489
87. Suzuki: Gooßen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458
88. Uhlig, E.; Bernd, N. Z. Chem. 1981, 21, 451
89. Fischer, R.; Walther, D.; Kempe, R.; Sieler, J.; Schonecker, B. J. Organomet. Chem. 1993, 447, 131
90. Phapale, V. B.; Buñuel, E.; García-Iglesias, M.; Cárdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790
91. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175
92. Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem. Soc. 2013, 135, 12004
93. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192
94. Zhao, Y.; Weix, D. J. J. Am. Chem. Soc. 2014, 136, 48
95. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433
96. Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437
97. Schley, N. D.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 16588-16593
98. González-Bobes, R.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360
99. Powell, D. A.; Maki, T.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 510
100. Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138
101. Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022
102. Creutz, S. E.; Lotito, K. J.; Fu, G. C.; Peters, J. C. Science 2012, 338, 647
103. 2 with organometallic reagents, e.g., PhZnCl, is known to accelerate an oxidative coupling process: Jin, L.; Liu, C.; Liu, J.; Hu, F.; Lan, Y.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B.; Lei, A. J. Am. Chem. Soc. 2009, 131, 16656
104. Very recently, Weix reported a similar synthesis of an alkyl acyl-Ni(II)-Cl complex in a THF solution with similar observation that Zn is not necessary but may enhance the reaction rate, see: Wotal, A. C.; Ribson, R. D.; Weix, D. J. Organometallics 2014, 33, 5874
105. 2 may also enhance the solvent dielectric: McCann, L. C.; Organ, M. G. Angew. Chem., Int. Ed. 2014, 53, 4386