Nickel-Catalyzed Cyclopropanation with NMe4OTf and nBuLi

Angewandte Chemie - International Edition

Volumn 54, Issue 36, 2015, Pages 10670-10674

  Künzi, Stefan A ^a   Sarria Toro, Juan Manuel ^a   Den Hartog, Tim ^a,b   Chen, Peter ^a,c  

^a ETH ZURICH   (Switzerland)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

carbenes; cyclopropanation; nickel; ylides

Indexed keywords

ORGANIC COMPOUNDS;

CARBENES; CYCLOPROPANATION; DIAZOMETHANES; METHYLENE DONOR; TRIFLATES; UNACTIVATED OLEFINS; YLIDES;

NICKEL;

EID: 84940449197     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201505482     Document Type: Article

References (46)

1. V. Franzen, G. Wittig, Angew. Chem. 1960, 72, 417-417.
2. G. Wittig, D. Krauss, Justus Liebigs Ann. Chem. 1964, 679, 34-41.
3. We have summarized these historical events elsewhere, see: S. A. Künzi, J. M. Sarria Toro, T. den Hartog, P. Chen, Isr. J. Chem., DOI:.
4. M. Pasco, N. Gilboa, T. Mejuch, I. Marek, Organometallics 2013, 32, 942-950
5. "Cyclopropanation mediated by zinc organometallics":, A. B. Charette, in The Chemistry of Organozinc Compounds, Vol. 1 (Eds.:, Z. Rappoport, I. Marek,), Wiley, Chichester, 2006, pp. 237-286.
6. 2
7. R. McCrindle, D. W. J. Sneddon, Organomet. Chem. 1985, 282, 413-419
8. Y. V. Tomilov, A. B. Kostitsyn, O. M. Nefedov, Izv. Akad. Nauk SSSR Ser. Khim. 1987, 2878
9. E. V. Guseva, N. V. Volchkov, Y. V. Tomilov, O. M. Nefedov, Eur. J. Org. Chem. 2004, 3136-3144, and references therein
10. M. D. Khanova, R. M. Sultanova, S. S. Zlotskii, V. A. Dokichev, Y. V. Tomilov, Russ. Chem. Bull. 2005, 54, 1003-1007
11. S. E. Denmark, R. A. Stavenger, A.-M. Faucher, J. P. J. Edwards, Org. Chem. 1997, 62, 3375-3389
12. G.-H. Fang, Z.-J. Yan, M.-Z. Deng, Org. Lett. 2004, 6, 357-360
13. M. A. Emerzian, W. Davenport, J. Song, J. Li, I. Erden, Adv. Synth. Catal. 2009, 351, 999-1004.
14. 2:, A. Nakamura, T. Toshikatsu, M. Cowie, S. Otsuka, J. A. Ibers, J. Am. Chem. Soc. 1977, 99, 2108-2117. Only trace yields of cyclopropanes were obtained when alkyl- and aryl-substituted olefins were used. For an alternative Ni-catalyzed cyclopropanation using lithiated sulfones, see
15. Y. Gai, M. Julia, J.-N. Verpeaux, Synlett 1991, 56-57.
16. T. den Hartog, J. M. Sarria Toro, E. P. A. Couzijn, P. Chen, Chem. Commun. 2014, 50, 10604-10607.
17. J. M. Sarria Toro, T. den Hartog, P. Chen, Chem. Commun. 2014, 50, 10608-10610.
18. P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Vol. 1, Academic Press, New York, 1974.
19. 3 ligand is present.
20. 2] without an additional ligand showed identical behavior, see Supporting Information.
21. T. den Hartog, J. M. Sarria Toro, P. Chen, Org. Lett. 2014, 16, 1100-1103.
22. T. S. Stevens, E. M. Creighton, A. B. Gordon, M. MacNicol, J. Chem. Soc. 1928, 3193-3197.
23. X. Zhang, Z.-Y. Geng, Y.-C. Wang, W.-Q. Li, Z. Wang, F.-X. Liu, J. Mol. Struct.: THEOCHEM 2009, 893, 56-66.
24. G. Wittig, K. Schwarzenbach, Justus Liebigs Ann. Chem. 1961, 650, 1-20
25. H. Daniel, J. Paetsch, Chem. Ber. 1965, 98, 1915-1922
26. W. K. Musker, R. R. Stevens, Inorg. Chem. 1969, 8, 255-264.
27. V. K. Aggarwal, G. Y. Fang, J. P. H. Charmant, G. Meek, Org. Lett. 2003, 5, 1757-1760
28. K. Honda, H. Shibuya, H. Yasui, Y. Hoshino, S. Inoue, Bull. Chem. Soc. Jpn. 2008, 81, 142-147.
29. K.-R. Pörschke, K. Jonas, G. Wilke, R. Benn, R. Mynott, R. Goddard, C. Krüger, Chem. Ber. 1985, 118, 275-297
30. K.-R. Pörschke, G. Wilke, R. Mynott, Chem. Ber. 1985, 118, 298-312.
31. D. J. Mindiola, G. L. Hillhouse, J. Am. Chem. Soc. 2002, 124, 9976-9977
32. V. M. Iluc, G. L. Hillhouse, J. Am. Chem. Soc. 2014, 136, 6479-6488.
33. R. Waterman, G. L. Hillhouse, J. Am. Chem. Soc. 2003, 125, 13350-13351.
34. J. H. Merrifield, G.-Y. Lin, W. A. Kiel, J. A. Gladysz, J. Am. Chem. Soc. 1983, 105, 5811-5819
35. R. R. Schrock, P. R. Sharp, J. Am. Chem. Soc. 1978, 100, 2389-2399.
36. H. Fischer, J. Am. Chem. Soc. 1986, 108, 3925-3927
37. K.-S. Focsaneanu, J. C. Scaiano, Helv. Chim. Acta 2006, 89, 2473-2482.
38. K. Ziegler, E. Holzkamp, H. Breil, H. Martin, Angew. Chem. 1955, 67, 541-547.
39. A. Maercker, W. Theysohn, Justus Leibigs Ann. Chem. 1971, 747, 70-83
40. P. Tomboulian, D. Amick, S. Beare, K. Dumke, D. Hart, R. Hites, A. Metzger, R. Nowak, J. Org. Chem. 1973, 38, 322-325.
41. R. Noyori, H. Kawauchi, H. Takaya, Tetrahedron Lett. 1974, 15, 1749-1752.
42. R. H. Grubbs, A. Miyashita, J. Am. Chem. Soc. 1978, 100, 7418-7420
43. A. Miyashita, R. H. Grubbs, Tetrahedron Lett. 1981, 22, 1255-1256
44. A. Miyashita, M. Ohyoshi, H. Shitara, H. Nohira, J. Organomet. Chem. 1988, 338, 103-111
45. R. Grubbs, A. Miyashita, in Fundamental Research in Homogeneous Catalysis (Ed.:, M. Tsutsui,), Springer, New York, 1979, pp. 151-163.
46. K. D. Kitiachvili, D. J. Mindiola, G. L. Hillhouse, J. Am. Chem. Soc. 2004, 126, 10554-10555.