An Unusual Mechanism of a Palladium-Catalyzed Intramolecular Carbametalation. A Novel Palladium-Catalyzed Rearrangement

Journal of the American Chemical Society

Volumn 110, Issue 5, 1988, Pages 1636-1638

  Trost, Barry M ^a   Tanoury, Gerald J ^b  

^a STANFORD UNIVERSITY   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000874926     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00213a054     Document Type: Article

References (11)

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10. Electron-withdrawing ligands on the metal are known to accelerate 1, 1-reductive eliminations, see: Kurosawa, H.; Emoto, M. Chem. Lett. 1985, 1161. Kurosawa, H.; Emoto, M.; Urabe, A. Chem. Commun. 1984, 968. Numata, S.; Kurosawa, H. J. Organomet. Chem. 1977, 131, 301. Temple, J. S.; Riediker, M.; Schwartz, J. J. Am. Chem. soc. 1982. 104. 1310. (19) Crocianai, B.; Boschi, T.; Belluco, U. Inorg. Chem. 1970, 9, 2021. Bonati, F.; Minghetti, G.; Boschi, T.; Crociani, B. J. organomet. Chem. 1970, 25, 255. Miller, J. S.; Balch, A. L. Inorg. Chem. 1972, 11, 2069. Larkin, G. A.; Scott, R. P.; Wallbridge, M. G. H. J. Organomet. Chem. 1972, 37, C21. Busetto, L.; Pallazi, A.; Crociani, B.; Belluco, V.; Badley, E. M.; Kilby, B. J. L.; Richards, R. L. J. Chem. Soc., Dalton Trans. 1972, 1800. Davies, C. H.; Game, C. H.; Green, M.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1974, 357. Bartel, K.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1974, 13, 599. Cardin, D. J.; Cetinkaya, B.; Cetinkaya, E.; Lappert, M. F. J. Chem. Soc., Dalton Trans. 1973, 514. Clark, H. C.; Jablonski, C. R. Inorg. Chem. 1974, 13, 2213. Clark, H. C.; Fiess, P. L.; Wong, C. S. Can. J. Chem. 1977, 55, 177. For Pd-catalyzed reactions of diazo compounds that may proceed via carbene intermediates, see: Hoffmann, K. L.; Regitz, M. Tetrahedron Lett. 1983, 24, 5355. Bien, S.; Segal, Y. J. Org. Chem. 1977, 42, 1685. Bien, S.; Ovadia, D. J. Org. Chem. 1970, 35, 1028. Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695. Mende, U.; Raduchel, B.; Skuballa, W.; Vorbruggen, H. Tetrahedron Lett. 1975, 629. Also, see: Catellani, M.; Chiusoli, G. P. Tetrahedron Lett. 1983, 24, 4493.
11. In acetylene trimerizations to benzenes, unusual regioselectivity that arises by formal insertion into an acetylenic bond has been observed as very minor pathways. Whitesides, G. M.; Ehmann, W. J. J. Am. Chem. Soc. 1969, 91, 3800. Dietl, H.; Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93. Maitlis, P. M. J. Organomet. Chem. 1980, 200, 161.