Nickel-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Alkynes with Formic Acid through Catalytic CO Recycling

ACS Catalysis

Volumn 6, Issue 4, 2016, Pages 2501-2505

  Fu, Ming Chen ^a   Shang, Rui ^a,b   Cheng, Wan Min ^a   Fu, Yao ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

alkynes; carbon monoxide; formic acid; hydrocarboxylation; nickel

Indexed keywords

CARBON MONOXIDE; CARBOXYLIC ACIDS; FORMIC ACID; NICKEL; RECYCLING;

ALKYNES; CARBOXYLIC ACID ANHYDRIDES; CATALYTIC AMOUNTS; HIGH SELECTIVITY; HYDROCARBOXYLATION; INTERNAL ALKYNES; STEREO-SELECTIVE; UNSATURATED CARBOXYLIC ACIDS;

HYDROCARBONS;

EID: 84963631882     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b00276     Document Type: Article

References (48)

1. Ojima, I. Chem. Rev. 1988, 88, 1011-1030 10.1021/cr00089a002
2. Zhang, Y.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210-6212 10.1002/anie.201101341
3. Quintero-Duque, S.; Dyballa, K. M.; Fleischer, I. Tetrahedron Lett. 2015, 56, 2634-2650 10.1016/j.tetlet.2015.04.043
4. Fujihara, T.; Xu, T.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2011, 50, 523-527 10.1002/anie.201006292
5. Li, S. H.; Yuan, W. M.; Ma, S. M. Angew. Chem., Int. Ed. 2011, 50, 2578-2582 10.1002/anie.201007128
6. Wang, X. Q.; Nakajima, M.; Martin, R. J. Am. Chem. Soc. 2015, 137, 8924-8927 10.1021/jacs.5b05513
7. Chiusoli, G. P.; Cassar, L. Angew. Chem., Int. Ed. Engl. 1967, 6, 124-133 10.1002/anie.196701241
8. Roso-Levi, G.; Amer, I. J. Mol. Catal. A: Chem. 1996, 106, 51-56 10.1016/1381-1169(95)00260-X
9. Amer, I.; Alper, H. J. Organomet. Chem. 1990, 383, 573-577 10.1016/0022-328X(90)85154-Q
10. Derien, S.; Dunach, E.; Perichon, J. J. Am. Chem. Soc. 1991, 113, 8447-8454 10.1021/ja00022a037
11. Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345-3347 10.1021/ol016585z
12. Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936-14937 10.1021/ja8062925
13. Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254-15255 10.1021/ja806677w
14. Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1999, 64, 3975-3978 10.1021/jo982443f
15. Aoki, M.; Kaneko, M.; Izumi, S.; Ukai, K.; Iwasawa, N. Chem. Commun. 2004, 2568-2569 10.1039/b411802b
16. Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435-2452 10.1039/c0cs00129e
17. Boddien, A.; Loges, B.; Gärtner, F.; Torborg, C.; Fumino, K.; Junge, H.; Ludwig, R.; Beller, M. J. Am. Chem. Soc. 2010, 132, 8924-8934 10.1021/ja100925n
18. Boddien, A.; Mellmann, D.; Gärtner, F.; Jackstell, R.; Junge, H.; Dyson, P. J.; Laurenczy, G.; Ludwig, R.; Beller, M. Science 2011, 333, 1733-1736 10.1126/science.1206613
19. Grasemann, M.; Laurenczy, G. Energy Environ. Sci. 2012, 5, 8171-8181 10.1039/c2ee21928j
20. Choudhary, V.; Mushrif, S. H.; Ho, C.; Anderko, A.; Nikolakis, V.; Marinkovic, N. S.; Frenkel, A. I.; Sandler, S. I.; Vlachos, D. G. J. Am. Chem. Soc. 2013, 135, 3997-4006 10.1021/ja3122763
21. Behr, A.; Nowakowski, K. Adv. Inorg. Chem. 2014, 66, 223-258 10.1016/B978-0-12-420221-4.00007-X
22. Tamaki, Y.; Koike, K.; Ishitani, O. Chem. Sci. 2015, 6, 7213-7221 10.1039/C5SC02018B
23. Chen, L. J.; Guo, Z.-G.; Wei, X.-G.; Gallenkamp, C.; Bonin, J.; Anxolabéhere-Mallart, E.; Lau, K. C.; Lau, T.-C.; Robert, M. J. Am. Chem. Soc. 2015, 137, 10918-10921 10.1021/jacs.5b06535
24. For selected reviews, see: Behr, A.; Nowakowski, K. Catalytic Hydrogenation of Carbon Dioxide to Formic Acid. In Adv. Inorg. Chem.; Aresta, M.; Eldik, R. V., Eds.; Academic Press: Waltham, 2014; Vol. 66, p 223.
25. 2 recycling, see: Zhu, C.; Takaya, J.; Iwasawa, N. Org. Lett. 2015, 17, 1814-1817 10.1021/acs.orglett.5b00692
26. Shen, R.; Chen, T.; Zhao, Y.; Qiu, R.; Zhou, Y.; Yin, S.; Wang, X.; Goto, M.; Han, L.-B. J. Am. Chem. Soc. 2011, 133, 17037-17044 10.1021/ja2069246
27. Ogoshi, S.; Ikeda, H.; Kurosawa, H. Angew. Chem., Int. Ed. 2007, 46, 4930-4932 10.1002/anie.200700688
28. Ohashi, M.; Hoshimoto, Y.; Ogoshi, S. Dalton Trans. 2015, 44, 12060-12073 10.1039/C5DT00640F
29. Fife, W. K.; Zhang, Z.-D. J. Org. Chem. 1986, 51, 3744-3746 10.1021/jo00369a048
30. Hou, J.; Xie, J.-H.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2015, 54, 6302-6305 10.1002/anie.201501054
31. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Org. Lett. 2003, 5, 4269-4272 10.1021/ol0354371
32. Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580-5588 10.1002/anie.200301736
33. Wang, Y.; Ren, W.-L.; Li, J.-F.; Wang, H.-N.; Shi, Y. Org. Lett. 2014, 16, 5960-5963 10.1021/ol502987f
34. El Ali, B.; Vasapollo, G.; Alper, H. J. Org. Chem. 1993, 58, 4739-4741 10.1021/jo00069a045
35. Zargarian, D.; Alper, H. Organometallics 1993, 12, 712-724 10.1021/om00027a022
36. Basolo, F.; Wojcicki, A. J. Am. Chem. Soc. 1961, 83, 520-525 10.1021/ja01464a003
37. Blomberg, M. R. A.; Brandemark, U. B.; Siegbahn, P. E. M.; Wennerberg, J.; Bauschlicher, C. W. J. Am. Chem. Soc. 1988, 110, 6650-6655 10.1021/ja00228a008
38. Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498-4499 10.1021/jo960410z
39. Hoshimoto, Y.; Ohata, T.; Sasaoka, Y.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2014, 136, 15877-15880 10.1021/ja509171a
40. Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573-13576 10.1021/ja306062c
41. Lu, Q.-Q.; Yu, H.-Z.; Fu, Y. J. Am. Chem. Soc. 2014, 136, 8252-8260 10.1021/ja4127455
42. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102 10.1021/ar9502341
43. Yu, J.-Q.; Spencer, J. B. Chem. Commun. 1998, 1935-1936 10.1039/a803809k
44. Bartoszewicz, A.; Ahlsten, N.; Martin-Matute, B. Chem.-Eur. J. 2013, 19, 7274-7302 10.1002/chem.201202836
45. Yang, P.; Xu, H.-Y.; Zhou, J.-R. Angew. Chem., Int. Ed. 2014, 53, 12210-12213 10.1002/anie.201407744
46. Xu, H.-Y.; Yang, P.; Chuanprasit, P.; Hirao, H.; Zhou, J.-R. Angew. Chem., Int. Ed. 2015, 54, 5112-5116 10.1002/anie.201501018
47. Iizuka, M.; Kondo, Y. Chem. Commun. 2006, 1739-1741 10.1039/b600632a
48. Takimoto, M.; Usami, S.; Hou, Z.-M. J. Am. Chem. Soc. 2009, 131, 18266-18268 10.1021/ja909126k