Rhodium(III)-catalyzed intramolecular hydroarylation, amidoarylation, and heck-type reaction: Three distinct pathways determined by an amide directing group

Angewandte Chemie - International Edition

Volumn 52, Issue 52, 2013, Pages 14181-14185

  Davis, Tyler A ^a   Hyster, Todd K ^a   Rovis, Tomislav ^a  

^a Department of Ecosystem Science and Sustainability   (United States)

Author keywords

amidoarylation; C H activation; Heck type reaction; hydroarylation; rhodium

Indexed keywords

AMIDOARYLATION; C-H ACTIVATION; CATALYZED REACTIONS; CONTIGUOUS STEREOCENTERS; DIRECTING GROUPS; HECK-TYPE REACTION; HYDROARYLATION; QUATERNARY CENTERS;

ACTIVATION ANALYSIS; CATALYSIS; RHODIUM;

AMIDES;

AMIDE; RHODIUM;

AMIDOARYLATION; ARTICLE; C-H ACTIVATION; CATALYSIS; CHEMISTRY; HECK-TYPE REACTION; HYDROARYLATION;

AMIDOARYLATION; C-H ACTIVATION; HECK-TYPE REACTION; HYDROARYLATION; RHODIUM;

AMIDES; CATALYSIS; RHODIUM;

EID: 84890739109     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307631     Document Type: Article

References (42)

1. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
2. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
3. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
4. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350
5. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
6. Angew. Chem. Int. Ed. 2011, 50, 1064
7. F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430.
8. T. K. Hyster, L. Knörr, T. R. Ward, T. Rovis, Science 2012, 338, 500
9. B. Ye, N. Cramer, Science 2012, 338, 504
10. B. Ye, N. Cramer, J. Am. Chem. Soc. 2013, 135, 636.
11. B. Li, J. Ma, N. Wang, H. Feng, S. Xu, B. Wang, Org. Lett. 2012, 14, 736; for an example with allenes, see
12. H. Wang, F. Glorius, Angew. Chem. 2012, 124, 7430
13. II catalyst and alkynes, see
14. B. Li, H. Feng, S. Xu, B. Wang, Chem. Eur. J. 2011, 17, 12573
15. L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. 2011, 123, 6503
16. Angew. Chem. Int. Ed. 2011, 50, 6379
17. L. Ackermann, S. Fenner, Org. Lett. 2011, 13, 6548.
18. R. K. Thalji, K. A. Ahrendt, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2001, 123, 9692
19. K. A. Ahrendt, R. G. Bergman, J. A. Ellman, Org. Lett. 2003, 5, 1301
20. R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192
21. R. K. Thalji, K. A. Ahrendt, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2005, 70, 6775
22. S. J. O'Malley, K. L. Tan, A. Watzke, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2005, 127, 13496
23. A. Watzke, R. M. Wilson, S. J. O'Malley, R. G. Bergman, J. A. Ellman, Synlett 2007, 2383
24. H. Harada, R. K. Thalji, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2008, 73, 6772. For an intramolecular Pd-catalyzed hydroarylation of indoles, see
25. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578; for an intramolecular cobalt-catalyzed hydroarylation of indoles, see
26. Z. Ding, N. Yoshikai, Angew. Chem. 2013, 125, 8736
27. III, see
28. X. Xu, Y. Liu, C.-M. Park, Angew. Chem. 2012, 124, 9506
29. Angew. Chem. Int. Ed. 2012, 51, 9372.
30. T. K. Hyster, T. Rovis, J. Am. Chem. Soc. 2010, 132, 10565.
31. I-catalyzed examples
32. S.-G. Lim, J.-A. Ahn, C.-H. Jun, Org. Lett. 2004, 6, 4687
33. C.-H. Jun, J.-B. Hong, Y.-H. Kim, K.-Y. Chung, Angew. Chem. 2000, 112, 3582
34. Angew. Chem. Int. Ed. 2000, 39, 3440.
35. L. Yang, C. A. Correia, C.-J. Li, Org. Biomol. Chem. 2011, 9, 7176
36. L. Yang, B. Qian, H. Huang, Chem. Eur. J. 2012, 18, 9511.
37. F. Yang, L. Ackermann, Org. Lett. 2013, 15, 718
38. Y. Wang, C. Li, Y. Li, F. Yin, X.-S. Wang, Adv. Synth. Catal. 2013, 355, 1724.
39. Y. J. Zhang, E. Skucas, M. J. Krische, Org. Lett. 2009, 11, 4248.
40. R. Zeng, C. Fu, S. Ma, J. Am. Chem. Soc. 2012, 134, 9597
41. H. Wang, N. Schröder, F. Glorius, Angew. Chem. 2013, 125, 5495
42. Angew. Chem. Int. Ed. 2013, 52, 5386.