Iron pincer complex catalyzed, environmentally benign, E-selective semi-hydrogenation of alkynes

Angewandte Chemie - International Edition

Volumn 52, Issue 52, 2013, Pages 14131-14134

  Srimani, Dipankar ^a   Diskin Posner, Yael ^a   Ben David, Yehoshoa ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

alkynes; homogeneous catalysis; hydrogenation; iron pincer complex; stereoselectivity

Indexed keywords

ALKYNES; ENVIRONMENTALLY BENIGN; ENVIRONMENTALLY BENIGN REACTION; HOMOGENEOUS CATALYSIS; IRON CATALYST; PINCER COMPLEXES; STEREO-SELECTIVE;

CATALYSIS; CATALYSTS; FUNCTIONAL GROUPS; HYDROCARBONS; HYDROGENATION; IRON; REACTION KINETICS; STEREOSELECTIVITY;

IRON COMPOUNDS;

EID: 84890631089     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306629     Document Type: Article

References (49)

1. J. G. de Vries, C. J. Elsevier, C. J. Handbook for Homogeneous Hydrogenation, Vol. 1, Wiley-VCH, Weinheim, 2007, p. 375.
2. D. J. Ager, in Handbook for Homogeneous Hydrogenation, Vol. 2, 1 st ed., (Eds.: J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, pp. 745.
3. H.-U. Blaser, A. Schnyder, H. Steiner, F. Rössler, P. Baumeister, in Handbook of Heterogeneous Catalysis, Vol. 7, 2 nd ed., (Eds.: G. Ertl, H. Knözinger, F. Schüth, J. Weitkamp,), Wiley-VCH, Weinheim, 2008, p. 3284.
4. H. Lindlar, R. Dubuis, Org. Synth. 1966, 46, 89.
5. D. J. Pasto, in Comprehensive Organic Synthesis Vol. 8 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, p. 471.
6. C. E. Castro, R. D. Stephens, J. Am. Chem. Soc. 1964, 86, 4358
7. A. B. Smith III, P. A. Levenberg, J. Z. Suits, Synthesis 1986, 184.
8. K. Tani, A. Iseki, T. Yamagata, Chem. Commun. 1999, 1821
9. B. M. Trost, Z. T. Ball, T. Jöge, J. Am. Chem. Soc. 2002, 124, 7922
10. E. Shirakawa, H. Otsuka, T. Hayashi, Chem. Commun. 2005, 5885
11. F. Luo, C. Pan, W. Wang, Z. Ye, J. Cheng, Tetrahedron 2010, 66, 1399
12. R. Shen, T. Chen, Y. Zhao, R. Qiu, Y. Zhou, S. Yin, X. Wang, M. Goto, L.-B. Han, J. Am. Chem. Soc. 2011, 133, 17037
13. D. Schleyer, H. G. Niessen, J. Bargon, New J. Chem. 2001, 25, 423
14. K. Radkowski, B. Sundararaju, A. Fürstner, Angew. Chem. 2013, 125, 373
15. Angew. Chem. Int. Ed. 2013, 52, 355.
16. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217
17. A. Correa, O. G. Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108
18. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500
19. S. Gaillard, J.-L. Renaud, ChemSusChem 2008, 1, 505
20. S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363
21. Angew. Chem. Int. Ed. 2008, 47, 3317
22. M. S. Chen, M. C. White, Science 2007, 318, 78.
23. R. Langer, G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 2168
24. Angew. Chem. Int. Ed. 2011, 50, 2120
25. R. Langer, Y. Diskin-Posner, G. Leitus, L. J. W. Shimon, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 10122
26. Angew. Chem. Int. Ed. 2011, 50, 9948
27. R. Langer, M. A. Iron, L. Konstantinovski, Y. Diskin-Posner, G. Leitus, Y. Ben-David, D. Milstein, Chem. Eur. J. 2012, 18, 7196
28. T. Zell, B. Butschke, Y. Ben-David, D. Milstein, Chem. Eur. J. 2013, 19, 8068
29. J. Zhang, M. Gandelman, D. Herrman, G. Leitus, L. J. W. Shimon, Y. Ben-David, D. Milstein, Inorg. Chim. Acta 2006, 359, 1955.
30. A. A. Mikhailine, M. I. Maishan, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2012, 134, 12266
31. A. Mikhailine, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2009, 131, 1394
32. A. A. Mikhailine, M. I. Maishan, R. H. Morris, Org. Lett. 2012, 14, 4638
33. A. M. Tondreau, C. Milsmann, A. D. Patrick, H. M. Hoyt, E. Lobkovsky, K. Wieghardt, P. J. Chirik, J. Am. Chem. Soc. 2010, 132, 15046
34. K. T. Sylvester, P. J. Chirik, J. Am. Chem. Soc. 2009, 131, 8772
35. M. M. Rodriguez, E. Bill, W. W. Brennessel, P. L. Holland, Science 2011, 334, 780
36. R. E. Cowley, N. A. Eckert, S. Vaddadi, T. M. Figg, T. R. Cundari, P. L. Holland, J. Am. Chem. Soc. 2011, 133, 9796
37. L.-Q. Lu, Y. Li, K. Junge, M. Beller, Angew. Chem. 2013, 125, 8540
38. Angew. Chem. Int. Ed. 2013, 52, 8382
39. S. Das, B. Wendt, K. Möller, K. Junge, M. Beller, Angew. Chem. 2012, 124, 1694
40. Angew. Chem. Int. Ed. 2012, 51, 1662.
41. C. Gunanathan, D. Milstein, Acc. Chem. Res. 2011, 44, 588
42. C. Gunanathan, D. Milstein, Science 2013, 341, DOI:.
43. C. Belger, B. Plietker, Chem. Commun. 2012, 48, 5419.
44. G. Wienhöfer, F. A. Westerhaus, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, Chem. Commun. 2012, 48, 4827.
45. S. C. Bart, E. Lobkovsky, P. J. Chirik, J. Am. Chem. Soc. 2004, 126, 13794.
46. S. Hillebrand, B. Bartkowska, J. Bruckmann, C. Kriiger, M. W. Haenel, Tetrahedron Lett. 1998, 39, 813.
47. Y. Yu, A. R. Sadique, J. M. Smith, T. R. Dugan, R. E. Cowley, W. W. Brennessel, C. J. Flaschenriem, E. Bill, T. R. Cundari, P. L. Holland, J. Am. Chem. Soc. 2008, 130, 6624.
48. R. Bau, H. S. H. Yuan, M. V. Baker, L. D. Field, Inorg. Chim. Acta 1986, 114, L27.
49. E. L. Smith, D. Sadowsky, C. J. Cramer, J. A. Phillips, J. Phys. Chem. A 2011, 115, 1955.