Functionalization of Unactivated C(sp3)−H Bonds Using Metal-Carbene Insertion Reactions

Angewandte Chemie - International Edition

Volumn 56, Issue 1, 2017, Pages 46-48

  Peña López, Miguel ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

carbenes; C H functionalization; diazo compounds; palladium; rhodium

Indexed keywords

EID: 85003856243     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201609033     Document Type: Article

References (44)

1. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998, chap. 4 and 5;
2. S.-F. Zhu, Q.-L. Zhou, Nat. Sci. Rev. 2014, 1, 580–603;
3. X. Zhao, Y. Zhang, J. Wang, Chem. Commun. 2012, 48, 10162–10173;
4. Y. Zhang, J. Wang, Eur. J. Org. Chem. 2011, 1015–1026;
5. A. G. H. Wee, Curr. Org. Synth. 2006, 3, 499–555.
6. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861–2903.
7. L. Liu, J. Zhang, Chem. Soc. Rev. 2016, 45, 506–516;
8. A. Ford, H. Miel, A. Ring, C. N. Slattery, A. R. Maguire, M. A. McKervey, Chem. Rev. 2015, 115, 9981–10080;
9. Y. Zhang, J. Wang, Chem. Commun. 2009, 5350–5361;
10. H. M. L. Davies, J. R. Denton, Chem. Soc. Rev. 2009, 38, 3061–3071;
11. Z. Zhang, J. Wang, Tetrahedron 2008, 64, 6577–6605;
12. T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091–1160;
13. A. Padwa, D. J. Austin, Angew. Chem. Int. Ed. Engl. 1994, 33, 1797–1815;
14. Angew. Chem. 1994, 106, 1881–1899.
15. For a general review on Wolff rearrangement, see:
16. W. Kirmse, Eur. J. Org. Chem. 2002, 2193–2256; For a review on ketenes as reactive intermediates, see:
17. A. D. Allen, T. T. Tidwell, Chem. Rev. 2013, 113, 7287–7342.
18. H. Pellissier, Tetrahedron 2008, 64, 7041–7095;
19. H. M. L. Davies, E. G. Antoulinakis, Org. React. 2004, 57, 1–326;
20. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977–1050.
21. S. E. Reisman, R. R. Nani, S. Levin, Synlett 2011, 2437–2442;
22. O. A. McNamara, A. R. Maguire, Tetrahedron 2011, 67, 9–40.
23. A. Caballero, M. M. Díaz-Requejo, M. R. Fructos, A. Olmos, J. Urbano, P. J. Pérez, Dalton Trans. 2015, 44, 20295–20307;
24. B. Xu, M.-L. Li, X.-D. Zuo, S.-F. Zhu, Q.-L. Zhou, J. Am. Chem. Soc. 2015, 137, 8700–8703;
25. S. Jia, D. Xing, D. Zhang, W. Hu, Angew. Chem. Int. Ed. 2014, 53, 13098–13101;
26. Angew. Chem. 2014, 126, 13314–13317.
27. H. Daorui, C. Shenxin, Z. Xueyan, Y. Qiuhan, Y. Qizheng, D. Zhenya, Austin J. Anal. Pharm. Chem. 2016, 3, 1064;
28. D. Gillingham, N. Fei, Chem. Soc. Rev. 2013, 42, 4918–4931;
29. S.-F. Zhu, Q.-L. Zhou, Acc. Chem. Res. 2012, 45, 1365–1377.
30. J. V. Santiago, A. H. L. Machado, Beilstein J. Org. Chem. 2016, 12, 882–902;
31. H. M. L. Davies, D. Morton, Chem. Soc. Rev. 2011, 40, 1857–1869;
32. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704–724;
33. H. M. L. Davies, A. R. Dick, Top. Curr. Chem. 2010, 292, 303–345;
34. C. N. Slattery, A. Ford, A. R. Maguire, Tetrahedron 2010, 66, 6681–6705;
35. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417–424.
36. H. M. L. Davies, T. Hansen, J. Am. Chem. Soc. 1997, 119, 9075–9076.
37. K. Liao, S. Negretti, D. G. Musaev, J. Bacsa, H. M. L. Davies, Nature 2016, 533, 230–234.
38. C. M. Quin, H. M. L. Davies, J. Am. Chem. Soc. 2014, 136, 9792–9796;
39. D. M. Guptill, H. M. L. Davies, J. Am. Chem. Soc. 2014, 136, 17718–17721.
40. B. Wang, D. Qiu, Y. Zhang, J. Wang, Beilstein J. Org. Chem. 2016, 12, 796–804;
41. F. Hu, Y. Xia, C. Ma, Y. Zhang, J. Wang, Chem. Commun. 2015, 51, 7986–7995;
42. Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res. 2013, 46, 236–247;
43. Y. Xia, Y. Zhang, J. Wang, ACS Catal. 2013, 3, 2586–2598.
44. A. Gutiérrez-Bonet, F. Juliá-Hernández, B. de Luis, R. Martin, J. Am. Chem. Soc. 2016, 138, 6384–6387.