The Renaissance of an Old Problem: Highly Regioselective Carboxylation of 2-Alkynyl Bromides with Carbon Dioxide

Chemistry - A European Journal

Volumn 21, Issue 48, 2015, Pages 17224-17228

  Miao, Bukeyan ^a   Li, Gen ^b   Ma, Shengming ^b,c  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

allenylation; carbon dioxide fixation; propargylation; regioselectivity; zinc

Indexed keywords

ATMOSPHERIC PRESSURE; CARBOXYLATION; REGIOSELECTIVITY; ZINC;

ALLENYLATION; CARBON DIOXIDE FIXATION; PROPARGYLATION; REACTION PARAMETERS; REGIOSELECTIVE CARBOXYLATION; STERIC EFFECT;

CARBON DIOXIDE;

EID: 84954402237     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503494     Document Type: Article

References (71)

1. The Chemistry of Ketenes, Allenes, and Related Compounds, Part 1 (Ed.:, S. Patai,), Wiley, New York, 1980;
2. H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley, New York, 1984;
3. The Chemistry of the Allenes, Vol. 1 (Ed.:, S. R. Landor,), Academic Press, London, 1982;
4. Modern Allene Chemistry, Vols. 1-2 (Eds.:, N. Krause, A. S. K. Hashmi,), Wiley-VCH, Weinheim, 2004;
5. Handbook of Cyclization Reactions, Vol. 1 (Ed.:, S. Ma,) Wiley-VCH, Weinheim, 2010.
6. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067;
7. A. Hoffmann-Röder, N. Krause, Angew. Chem. Int. Ed. 2004, 43, 1196;
8. Angew. Chem. 2004, 116, 1216;
9. S. Ma, Chem. Rev. 2005, 105, 2829;
10. S. Ma, Acc. Chem. Res. 2003, 36, 701;
11. J. Ye, S. Ma, Acc. Chem. Res. 2014, 47, 989.
12. S. Ma, Z. Shi, L. Li, J. Org. Chem. 1998, 63, 4522;
13. S. Ma, Z. Shi, J. Org. Chem. 1998, 63, 6387;
14. S. Ma, Z. Yu, S. Wu, Tetrahedron 2001, 57, 1585;
15. S. Ma, Z. Yu, Angew. Chem. Int. Ed. 2002, 41, 1775;
16. Angew. Chem. 2002, 114, 1853;
17. S. Ma, Z. Yu, Org. Lett. 2003, 5, 1507;
18. S. Ma, Z. Yu, Angew. Chem. Int. Ed. 2003, 42, 1955;
19. Angew. Chem. 2003, 115, 1999;
20. S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149;
21. S. Ma, Z. Yu, Z. Gu, Chem. Eur. J. 2005, 11, 2351;
22. S. Ma, Z. Gu, J. Am. Chem. Soc. 2005, 127, 6182;
23. Z. Gu, S. Ma, Angew. Chem. Int. Ed. 2006, 45, 6002;
24. Angew. Chem. 2006, 118, 6148.
25. R. Lü, X. Cheng, X. Zheng, S. Ma, Chem. Commun. 2014, 50, 1537.
26. S. Ma, S. Wu, J. Org. Chem. 1999, 64, 9314;
27. S. Ma, S. Wu, Chem. Commun. 2001, 441.
28. J. A. Marshall, E. D. Robinson, A. Zapata, J. Org. Chem. 1989, 54, 5854;
29. C. Li, X. Wang, X. Sun, Y. Tang, J. Zheng, Z. Xu, Y. Zhou, L. Dai, J. Am. Chem. Soc. 2007, 129, 1494.
30. J. A. Marshall, M. A. Wolf, J. Org. Chem. 1996, 61, 3238;
31. J. A. Marshall, M. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367;
32. Y. Wang, W. Zhang, S. Ma, Org. Chem. Front. 2014, 1, 807;
33. Y. Wang, S. Ma, Adv. Synth. Catal. 2013, 355, 741.
34. Y. Wang, W. Zhang, S. Ma, J. Am. Chem. Soc. 2013, 135, 11517.
35. J. Louie, Curr. Org. Chem. 2005, 9, 605;
36. T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365;
37. M. Aresta, A. Dibenedetto, Dalton Trans. 2007, 2975;
38. A. Correa, R. Martin, Angew. Chem. Int. Ed. 2009, 48, 6201;
39. Angew. Chem. 2009, 121, 6317;
40. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347;
41. C. Federsel, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2010, 49, 6254;
42. Angew. Chem. 2010, 122, 6392;
43. K. Huang, C. Sun, Z. Shi, Chem. Soc. Rev. 2011, 40, 2435;
44. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kuhn, Angew. Chem. Int. Ed. 2011, 50, 8510;
45. Angew. Chem. 2011, 123, 8662.
46. P. H. Lee, H. Kim, K. Lee, M. Kim, K. Noh, H. Kim, D. Seomoon, Angew. Chem. Int. Ed. 2005, 44, 1840;
47. Angew. Chem. 2005, 117, 1874;
48. P. H. Lee, H. Kim, K. Lee, Adv. Synth. Catal. 2005, 347, 1219;
49. C. Park, P. H. Lee, Org. Lett. 2008, 10, 3359;
50. S. Kim, K. Lee, D. Seomoon, P. H. Lee, Adv. Synth. Catal. 2007, 349, 2449;
51. L. Guo, H. Gao, P. Mayer, P. Knochel, Chem. Eur. J. 2010, 16, 9829;
52. J. Park, S. H. Kim, P. H. Lee, Org. Lett. 2008, 10, 5067;
53. T. Hirashita, Y. Suzuki, H. Tsuji, Y. Sato, K. Naito, S. Araki, Eur. J. Org. Chem. 2012, 5668.
54. L. W. Bieber, M. F. D. Silva, R. C. D. Costa, L. O. S. Silva, Tetrahedron Lett. 1998, 39, 3655;
55. F. Barbot, Ph. Miginiac, J. Organomet. Chem. 1992, 440, 249;
56. J. Muñoz-Bascõn, I. Sancho-Sanz, E. Alvare-Manzaneda, A. Rosales, J. E. Oltra, Chem. Eur. J. 2012, 18, 14479.
57. J. H. Ford, C. D. Thompson, C. S. Marvel, J. Am. Chem. Soc. 1935, 57, 2619;
58. J. C. Clinet, G. Linstrumelle, Synthesis 1981, 875.
59. E. Favre, M. Gaudemar, J. Organomet. Chem. 1974, 76, 297;
60. E. Favre, M. Gaudemar, J. Organomet. Chem. 1974, 76, 305;
61. X. Creary, J. Am. Chem. Soc. 1977, 99, 7632;
62. N. R. Pearson, G. Hahn, G. Zweifel, J. Org. Chem. 1982, 47, 3364;
63. S. Ma, A. Zhang, J. Org. Chem. 2002, 67, 2287;
64. S. Ma, A. Zhang, Y. Yu, W. Xia, J. Org. Chem. 2000, 65, 2287.
65. C. Feng, T.-P. Loh, Angew. Chem. Int. Ed. 2013, 52, 12414;
66. Angew. Chem. 2013, 125, 12640.
67. For a pioneering report on cobalt-catalyzed carboxylation of propargylic acetates with the help of Mn powder forming 3-alkynoic acids with substrates bearing a bulky tBu and TMS substituent at the sp carbon atom, see:, K. Nogi, T. Fujihara, J. Terao, Y. Tsuji, Chem. Commun. 2014, 50, 13052.
68. A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. Int. Ed. 2006, 45, 6040;
69. Angew. Chem. 2006, 118, 6186.
70. J. Bejjani, C. Botuha, F. Chemla, F. Ferreira, S. Magnus, A. Perez-Luna, Organometallics 2012, 31, 4876.
71. B. W. Gung, X. Xue, N. Knatz, J. A. Marshall, Organometallics 2003, 22, 3158.