The isolation and characterization of a rhodacycle intermediate implicated in metal-catalyzed reactions of alkylidenecyclopropanes

Angewandte Chemie - International Edition

Volumn 53, Issue 15, 2014, Pages 3952-3956

  Inglesby, Phillip A ^a   Bacsa, John ^a   Negru, Daniela E ^b   Evans, P Andrew ^b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b QUEEN S UNIVERSITY   (Canada)

Author keywords

carbocyclization; ene cycloisomerization; reactive intermediates; rhodium; allyl ligands

Indexed keywords

CATALYSIS; ISOMERIZATION; RHODIUM; SELF ASSEMBLY; X RAY CRYSTALLOGRAPHY;

ALKYLIDENECYCLOPROPANES; ALLYL LIGANDS; CARBOCYCLIZATION; CARBOCYCLIZATION REACTIONS; ENE-CYCLOISOMERIZATION; ISOLATION AND CHARACTERIZATION; REACTIVE INTERMEDIATE; RHODIUM-CATALYZED;

REACTION INTERMEDIATES;

EID: 84898060233     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310232     Document Type: Article

References (27)

1. P. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791-2805
2. C. Aubert, M. Malacria, C. Ollivier, in Science of Synthesis, Vol. 3 (Eds.:, J. G. de Vries, G. A. Molander, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 145-242, and pertinent references therein.
3. W. Reppe, W. J. Schweckendiek, Justus Liebigs Ann. Chem. 1948, 560, 104-116.
4. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179
5. H. Pellissier, Tetrahedron 2010, 66, 8341-8375.
6. A. Masarwa, I. Marek, Chem. Eur. J. 2010, 16, 9712-9721
7. C. Aïssa, Synthesis 2011, 3389-3407.
8. P. A. Evans, P. A. Inglesby, J. Am. Chem. Soc. 2008, 130, 12838-12839
9. S. Mazumder, D. Shang, D. E. Negru, M.-H. Baik, P. A. Evans, J. Am. Chem. Soc. 2012, 134, 20569-20572; For a highlight on the combination of computational studies with experimental results, see
10. I. Thiel, M. Hapke, Angew. Chem. 2013, 125, 6030-6032
11. Angew. Chem. Int. Ed. 2013, 52, 5916-5918.
12. P. A. Evans, P. A. Inglesby, J. Am. Chem. Soc. 2012, 134, 3635-3638.
13. For a recent review on transition-metal-catalyzed ene-cycloisomerization reactions, see:, I. D. G. Watson, F. D. Toste, in Science of Synthesis, Vol. 3 (Eds.:, J. G. de Vries, G. A. Molander, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 243-307, and pertinent references therein.
14. P. Binger, U. Schuchardt, Angew. Chem. 1977, 89, 254-255
15. Angew. Chem. Int. Ed. Engl. 1977, 16, 249-250
16. B. M. Trost, M. L. Miller, J. Am. Chem. Soc. 1988, 110, 3687-3689
17. M. Lautens, Y. Ren, J. Am. Chem. Soc. 1996, 118, 10668-10669
18. M. Gulías, R. García, A. Delgado, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2006, 128, 384-385.
19. For an example of the consequence of σ- vs. π-character on reductive elimination, see:, Y. Wang, J. Wang, J. Su, F. Huang, L. Jiao, Y. Liang, D. Yang, S. Zhang, P. A. Wender, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 10060-10061.
20. 2) reductive elimination, see:, S. Ikeda, Y. Maruyama, F. Ozawa, Organometallics 1998, 17, 3770-3774.
21. CCDC 954061 (2 a) contains 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.
22. H. Wang, F. Glorius, Angew. Chem. 2012, 124, 7430-7434
23. Angew. Chem. Int. Ed. 2012, 51, 7318-7322
24. D. N. Tran, N. Cramer, Angew. Chem. 2013, 125, 10824-10828
25. Angew. Chem. Int. Ed. 2013, 52, 10630-10634.
26. For a recent example of this type of transformation, see:, N. N. Noucti, E. J. Alexanian, Angew. Chem. 2013, 125, 8582-8585
27. Angew. Chem. Int. Ed. 2013, 52, 8424-8427.