The Dötz Reaction: A Chromium Fischer Carbene-Mediated Benzannulation Reaction

Author:

Solà Miquel,Duran Miquel,Torrent Maricel

Publisher

Springer US

Reference53 articles.

1. For reviews see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; VCH: Weinheim, 1983. (b) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Hegedus, L. S. Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, p. 549. (d) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p. 1065. (e) Wulff, W.D. Comprehensive Organometallic Chemistry II; Abel, E.W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, p. 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) de Meijere, A. Pure Appl. Chem. 1996, 68, 61. (h) Barluenga, J. Pure Appl. Chem. 1996, 68, 543. (i) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163. (j) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187. (k) Sierra, M. A. Chem. Rev. 2000, 100, 3591. (1) Davies, M. W.; Johnson, C. N.; Harrity, J. P. A. J. Org. Chem. 2001, 66, 3525. (m) Barluenga, J.; Suárez-Sobrino, A. L.; Tomás, M.; García-Granda, S.; Santiago-García, R. J. Am. Chem. Soc. 2001, 123, 10494.

2. (a) Schmalz, H.-G. Angew. Chem. 1994, 106, 311; Angew. Chem., Int. Ed. Engl. 1994, 33, 303. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2001, 123, 11113.

3. Dötz, K. H. Angew. Chem. 1975, 87, 672; Angew. Chem., Int. Ed. Engl. 1975, 14, 644.

4. (a) Dötz, K. H.; Dietz, R. Chem. Ber. 1978, 111, 2517. (b) Dötz, K. H.; Pruskil, I. Chem. Ber. 1980, 113, 2876. (c) Wulff, W. D.; Tang, P. C.; McCallum, J. S. J. Am. Chem. Soc. 1981, 103, 7677. (d) Dötz, K. H.; Mühlemeier, J.; Schubert, U.; Orama, O. J. Organomet. Chem. 1983, 247, 187. (e) Wulff, W. D.; Chan, K. S.; Tang, P. C. J. Org. Chem. 1984, 49, 2293. (f) Yamashita, A.; Toy, A. Tetrahedron Lett. 1986, 27, 3471.

5. Benzannulation with stannylalkynes shows the reversed regioselectivity: Chamberlain, S.; Waters, M. L.; Wulff, W. D. J. Am. Chem. Soc. 1994, 116, 3113.

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