Rhodium(I)-catalyzed decarbonylative spirocyclization through C=C bond cleavage of benzocyclobutenones: An efficient approach to functionalized spirocycles

Angewandte Chemie - International Edition

Volumn 53, Issue 7, 2014, Pages 1891-1895

  Xu, Tao ^a   Savage, Nikolas A ^a   Dong, Guangbin ^a  

^a University of Texas at Austin   (United States)

Author keywords

C=C activation; decarbonylation; homogeneous catalysis; rhodium; spirocycles

Indexed keywords

BOND CLEAVAGES; DECARBONYLATIONS; FUNCTIONALIZED; HOMOGENEOUS CATALYSIS; MECHANISTIC STUDIES; RHODIUM-CATALYZED; SPIROCYCLES; SPIROCYCLIZATION;

CARBON; CATALYSIS; FUNCTIONAL GROUPS; LIGANDS; OLEFINS; REACTION KINETICS;

RHODIUM;

BENZOCYCLOBUTENE; POLYCYCLIC HYDROCARBON; RHODIUM; SPIRO COMPOUND;

ARTICLE; C C ACTIVATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DECARBONYLATION; HOMOGENEOUS CATALYSIS; SPIROCYCLES; STEREOISOMERISM; SYNTHESIS;

C C ACTIVATION; DECARBONYLATION; HOMOGENEOUS CATALYSIS; RHODIUM; SPIROCYCLES;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; RHODIUM; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84893525485     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310149     Document Type: Article

References (50)

1. W. D. Jones, Nature 1993, 364, 676
2. M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97
3. B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918
4. Angew. Chem. Int. Ed. 1999, 38, 870
5. C. Perthuisot, B. L. Edelbach, D. L. Zubris, N. Simhai, C. N. Iverson, C. Müller, T. Satoh, W. D. Jones, J. Catal. Mol. A 2002, 189, 157
6. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759
7. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610
8. T. Satoh, M. Miura, Top. Organomet. Chem. 2005, 14, 1
9. C.-H. Jun, J. W. Park, Top. Organomet. Chem. 2007, 24, 117
10. D. Necas, M. Kotora, Curr. Org. Chem. 2007, 11, 1566
11. R. H. Crabtree, Chem. Rev. 1985, 85, 245
12. T. Kondo, T. A. Mitsudo, Chem. Lett. 2005, 34, 1462
13. K. Ruhland, Eur. J. Org. Chem. 2012, 2683
14. A. Korotvicka, D. Necas, M. Kotora, Curr. Org. Chem. 2012, 16, 1170
15. T. Seiser, T. Saget, D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 7884
16. Angew. Chem. Int. Ed. 2011, 50, 7740
17. M. Murakami, T. Matsuda, Chem. Commun. 2011, 47, 1100.
18. For a recent review of decarbonylative C=C forming reactions, see:, A. Dermenci, G. Dong, Sci. China Chem. 2013, 56, 685.
19. K. Kaneda, H. Azuma, M. Wayaku, S. Teranishi, Chem. Lett. 1974, 215
20. M. Murakami, H. Amii, Y. Ito, Nature 1994, 370, 540
21. M. Murakami, H. Amii, K. Shigeto, Y. Ito, J. Am. Chem. Soc. 1996, 118, 8285
22. T. Matsuda, M. Shigeno, M. Murakami, Chem. Lett. 2006, 35, 288
23. Z.-Q. Lei, H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, J. Sun, Z.-J. Shi, Angew. Chem. 2012, 124, 2744
24. Angew. Chem. Int. Ed. 2012, 51, 2690
25. A. Dermenci, R. E. Whittaker, G. Dong, Org. Lett. 2013, 15, 2242.
26. For an example of olefin formation through C=C activation/ decarbonylation/β-H elimination, see:, M. Murakami, T. Itahashi, Y. Ito, J. Am. Chem. Soc. 2002, 124, 13976, and ref. [3c].
27. K. Teruyuki, N. Ayoko, O. Takumi, S. Nobuyoshi, W. Kenji, M. Take-aki, J. Am. Chem. Soc. 2000, 122, 6319
28. T. Kondo, Y. Taguchi, Y. Kaneko, M. Niimi, T.-A. Mitsudo, Angew. Chem. 2004, 116, 5483
29. Angew. Chem. Int. Ed. 2004, 43, 5369
30. Y. Yamamoto, S. Kuwabara, H. Hayashi, H. Nishiyama, Adv. Synth. Catal. 2006, 348, 2493.
31. T. Xu, G. Dong, Angew. Chem. 2012, 124, 7685
32. Angew. Chem. Int. Ed. 2012, 51, 7567
33. T. Xu, H. M. Ko, N. A. Savage, G. Dong, J. Am. Chem. Soc. 2012, 134, 20005.
34. S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis 2009, 165, and references therein
35. M. Sannigrahi, Tetrahedron 1999, 55, 9007; for a seminal work on spirocycle formation initiated by C=H activation, see
36. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578
37. H. Zhang, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2004, 116, 6270
38. Angew. Chem. Int. Ed. 2004, 43, 6144.
39. seminal work:, X.-Z. Shu, S. Huang, D. Shu, I. A. Guzei, W. Tang, Angew. Chem. 2011, 123, 8303
40. Angew. Chem. Int. Ed. 2011, 50, 8153
41. a review:, X.-Z. Shu, D. Shu, C. M. Schienebeck, W. Tang, Chem. Soc. Rev. 2012, 41, 7698.
42. J. F. Hartwig, in Organotransition Metal Chemistry: from Bonding to Catalysis, University Science Books, Mill Valley, 2009
43. J. F. Hartwig, Inorg. Chem. 2007, 46, 1936.
44. For a recent review of transition-metal-catalyzed olefin isomerization, see:, K. Tanaka, in Comprehensive Organometallic Chemistry III, Vol. 10 (Eds.:, R. H. Crabtree, D. M. P. Mingos, I. Ojima,), Elsevier, Oxford, UK, 2007, p. 71.
45. M. Hatano, K. Mikami, J. Am. Chem. Soc. 2003, 125, 4704
46. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, Organometallics 1993, 12, 4188
47. O. Loiseleur, P. Meier, A. Pfaltz, Angew. Chem. 1996, 108, 218
48. Angew. Chem. Int. Ed. Engl. 1996, 35, 200.
49. D. Krois, E. Langer, H. Lehner, Tetrahedron 1980, 36, 1345.
50. CCDC 962877 (3 a), 962878 (3 c), and 962879 (3 d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.