Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1780-1783

  Nurhanna Riduan, Siti ^a   Ying, Jackie Y ^a   Zhang, Yugen ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON DIOXIDE; COPPER; SULFIDE; THIOL DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CARBON DIOXIDE; CATALYSIS; COPPER; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; SULFIDES; WATER;

EID: 84859609565     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3003699     Document Type: Article

References (55)

1. Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: Chichester, 1996.
2. Malyshev, D. A.; Scott, N. M.; Marion, N.; Stevens, E. D; Ananikov, V. P.; Beletskaya, I. P; Nolan, S. P. Organometallics 2006, 25, 4462-4470
3. Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L. Adv. Synth. Catal. 2005, 347, 1993-2001
4. Cao, C.; Fraser, L. R.; Love, J. A. J. Am. Chem. Soc. 2005, 127, 17614-17615
5. Fraser, L. R.; Bird, J.; Wu, Q.; Cao, C.; Patrick, B. O.; Love, J. A. Organometallics 2007, 26, 5601-5611
6. Yang, J.; Sabarre, A.; Fraser, L. R.; Patrick, B. O.; Love, J. A. J. Org. Chem. 2009, 74, 182-187
7. Weiss, C. J.; Wobser, S. D.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 2062-2063
8. Weiss, C. J.; Wobser, S. D.; Marks, T. J. Organometallics 2010, 29, 6308-6320
9. Weiss, C. J.; Marks, T. J. Dalton Trans. 2010, 39, 6576-6588
10. Weiss, C. J.; Marks, T. J. J. Am. Chem. Soc. 2010, 132, 10533-10546
11. Cabrero-Antonino, J. R.; Leyva-Pérez, A; Corma, A. Adv. Synth. Catal., DOI: 10.1002/adsc.201100731.
12. Leyva-Pérez, A.; Vidal-Moya, J. A.; Cabrero-Antonino, J. R.; Al-Deyab, S. S.; Al-Resayes, S. I.; Corma, A. J. Organomet. Chem. 2011, 696, 362-367
13. Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T. J. Am. Chem. Soc. 1999, 121, 5108-5114
14. Shoai, S.; Bichler, P.; Kang, B.; Buckley, H.; Love, J. A. Organometallics 2007, 26, 5778-5781
15. Yang, Y.; Rioux, R. M. Chem. Commun. 2011, 47, 6557-6559
16. Corma, A.; González-Aellano, C.; Igesias, M.; Sánchez, F. Appl. Catal., A 2010, 375, 49-54
17. Burling, S.; Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Dalton Trans. 2003, 4181-4191
18. Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Dalton Trans. 2009, 3599-3614
19. Truce, W. E.; Simms, J. A.; Boudakian, M. M. J. Am. Chem. Soc. 1956, 78, 695-696
20. Truce, W. E.; Simms, J. A. J. Am. Chem. Soc. 1956, 78, 2756-2759
21. Kondoh, A.; Takami, K.; Yorimitsu, H.; Oshima, K. J. Org. Chem. 2005, 70, 6468-6473
22. Griesbaum, K. Angew. Chem., Int. Ed. 1970, 9, 273-287
23. Wang, Z.-L.; Tang, R.-Y.; Luo, P.-S.; Deng, C.-L.; Zhong, P.; Li, J.-H. Tetrahedron 2008, 64, 10670-10675
24. Carbon Dioxide as Chemical Feedstock; Aresta, M., Ed.; Wiley-VCH: Weinheim, 2010.
25. 2 Conversion and Utilization; ACS Symposium Series 809; American Chemical Society: Washington, DC, 2002; pp 54-70.
26. Riduan, S. N.; Zhang, Y. Dalton Trans. 2010, 39, 3347-3357
27. Zhang, Y.; Chan, J. Y. G. Energy Environ. Sci. 2010, 3, 408-417
28. Sakakura, T.; Kohon, K. Chem. Commun. 2009, 1312-1330
29. Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365-2387
30. Marks, T. J. Chem. Rev. 2001, 101, 953-996
31. Coates, G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618-6639
32. Darensbourg, D. J. Chem. Rev. 2007, 107, 2388-2410
33. Behr, A.; Henze, G. Green Chem. 2011, 13, 25-39
34. Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435-2452
35. Zhang, Y.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210-6212
36. Zhang, L.; Cheng, J.; Ohishi, T.; Hou, Z. Angew. Chem., Int. Ed. 2010, 49, 8670-8674
37. Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792-5795
38. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem., Int. Ed. 2010, 49, 8674-8677
39. Mizuno, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 1251-1253
40. Correa, A.; Martin, R. J. Am. Chem. Soc. 2009, 131, 15974-15975
41. Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 14936-14937
42. Johnson, M. T.; Johansson, R.; Kondrashov, M. V.; Steyl, G.; Ahlquist, M. S. G.; Roodt, A.; Wendt, O. F. Organometallics 2010, 29, 3521-3529
43. Yu, D.; Zhang, Y. Green Chem. 2011, 13, 1275-1279
44. Riduan, S. N.; Zhang, Y.; Ying, J. Y. Angew. Chem., Int. Ed. 2009, 48, 3322-3325
45. Gu, L.; Zhang, Y. J. Am. Chem. Soc. 2010, 132, 914-915
46. Yu, D.; Zhang, Y. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20184-20189
47. Goossen, L. J.; Rodriguez, N.; Manjolinho, F.; Lange, P. P. Adv. Synth. Catal. 2010, 352, 2913-2917
48. Zhang, X.; Zhang, W. Z.; Ren, X.; Zhang, L. L.; Lu, X. B. Org. Lett. 2011, 13, 2402-2405
49. Nicolau, K. C.; Sarlah, D.; Shaw, D. M. Angew. Chem., Int. Ed. 2007, 46, 4708-4711
50. Ranjit, S.; Duan, Z.; Zhang, P.; Liu, X. Org. Lett. 2010, 12, 4134-4136
51. Taniguchi, T.; Fujii, T.; Idota, A.; Ishibashi, H. Org. Lett. 2009, 11, 3298-3301
52. Bieber, L. W.; da Silva, M. F.; Menezes, P. H. Tetrahedron Lett. 2004, 45, 2735-2737
53. Zhou, F.; Rosen, J.; Zebrowshi-Young, J. M.; Freihammer, P. M.; Detty, M. R.; Lachiotte, R. J. J. Org. Chem. 1998, 63, 5403-5412
54. Freihammer, P. M.; Detty, M. R. J. Org. Chem. 2000, 65, 7203-7207
55. Overberger, C. G.; Mallon, H. J.; Fine, R. J. Am. Chem. Soc. 1950, 72, 4958-4961