Carbene variations of some classical reactions
DOI:
https://doi.org/10.24959/zofh.17.909Keywords:
carbenes, reactions, catalysisAbstract
Carbene variations of a series of fundamental reactions, the features of their course in comparison with classical analogues have been first summarized and analyzed in the review. A number of carbene transformations described in the literature relates to classical name reactions being substantially their carbene variations acquiring the characteristics with the participation of carbenes. The attention in the review is drawn to such important analogies. Besides the carbene mechanism, they differ from the classical versions of the reactions because they mostly proceed under milder, sometimes considerably milder conditions. They always lead to specific products, the structure of which is conditioned by the nature of carbenes as ambiphilic reagents, and it affects certain stages and the final result of the reaction. In the above terms, such reactions are considered for the cases when carbenes are stoichiometrical components (carbene variations of Bodger, Michaelis-Arbuzov, Leuckart-Wallach reactions, Claisen condensation, Hoffman elimination), as well as for the cases when they are catalytic components (transesterification, Stetter reactions, benzoin condensation, nucleophilic aromatic substitution). At the present stage carbene variations of the classical reactions have become promising in the synthesis of some pharmaceutical substances, as well as in diesel fuel obtaining from vegetable oils. The review is intended to initiate further searches and deepening of such analogies.
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- Нефедов О.М., Иоффе А.И., Менчиков Л.Г. Химия карбенов. – М.: Химия, 1990. – C. 42-83.
- Roth H.D., Hutton R.S. // Tetrahedron. – 1985. – Vol. 41, №8. – Р. 1567-1578.
- Дьяконов И.А., Данилкина Л.П. // ЖОрХ. – 1966. – Т. 2, №1. – С. 3-11.
- Hartzler H.D. // J. Am. Chem. Soc. – 1973. – Vol. 95, №13. – P. 4379-4387.
- Coffen D.L. // Tetrahedron. Lett. – 1970. – №30. – P. 2633-2636.
- Kassam K., Warkentin J. // Can. J. Chem. – 1997. – Vol. 75. – P. 120-128.
- Couture P., Warkentin J. // Can. J. Chem. – 1997. – Vol. 75. – P. 1281-1294.
- Cheng Y., Zhu Q., Li Q.S., Meth-Cohn O. // J. Org. Chem. – 2005. – Vol. 70, №12. – P. 4840-4846.
- Nair V., Bindu S., Sreekumar V., Rath N.P. // Org. Lett. – 2003. – Vol. 5, №5. – P. 665-667.
- Bertrand G. (Ed.). Carbene Chemistry. From Fleeting Intermediates to Powerful Reagents. – New York: Foutis Media, Lausanne, 2002. – P. 153-199.
- Bourissou D., Guerret O., Gabbai F.P., Bertrand G. // Chem. Rev. – 2000. – Vol. 100, №1. – P. 39-91.
- Ли Дж. Дж. Именные реакции. Механизмы органических реакций. – М.: Бином. Лаборатория знаний, 2009. – 456 с.
- Enders D., Breuer K., Runsink J., Teles J.H. // Lieb. Ann. Chem. – 1996. – №12. – P. 2019-2028.
- Frenzen G., Kummel A., Meyer-Dutheuer C., Seitz G. // Chem. Ber. – 1994. – Vol. 127. – P. 1803-1806.
- Imming P., Kummell A., Seitz G. // Heterocycles. – 1993. – Vol. 35, №2. – P. 299-306.
- Bostai B., Novak Z., Benyei A.C., Kotschi A. // Org. Lett. – 2007. – Vol. 9, №17. – P. 3437-3439.
- Illa O., Gornitzka H., Baceiredo A. et al. // J. Org. Chem. – 2003. – Vol. 68, №20. – P. 7707-7710.
- Oda R., Ito Y., Okano M. // Tetrahedron Lett. – 1964. – №1. – P. 7-9.
- Seyfereth D., Grim S.O., Read N.O. // J. Am. Chem. Soc. – 1960. – Vol. 82, №6. – P. 1510.
- Speziale A.J., Ratts K.W. // J. Am. Chem. Soc. – 1962. – Vol. 84, №5. – P. 854-859.
- Speziale A.J., Marco G.J., Ratts K.W. // J. Am. Chem. Soc. – 1960. – Vol. 82, №5. – P. 1260.
- Сафиев О.Г., Назаров Д.В., Зорин В.В., Рахманкулов Д.Л. // ХГС. – 1988. – №6. – C. 852.
- Takamizawa A., Hirai K., Hamashima Y. // Tetrahedron Lett. – 1967. – №50. – P. 5081-5084.
- Korotkikh N.I., Cowley A.H., Moore J.A. et al. // Org. Biomol. Chem. – 2008. – Vol. 1, №1. – P. 195-199.
- Korotkikh N.I., Glinyanaya N.V., Cowley A.H. et al. // ARKIVOC. – 2007. – №16. – P. 156-172.
- Короткіх М.І., Раєнко Г.Ф., Швайка О.П. // Доп. НАН України. – 2001. – №11. – C. 130-133.
- Korotkikh N.I., Rayenko G.F., Kiselyov A.V. et al. // In: Selected Methods of Synthesis and Modifications of Heterocycles. – Moscow: Irridium-Press, 2002. – Vol. 1. – P. 220-240.
- Korotkikh N.I., Shvaika O.P., Rayenko G.F. et al. // ARKIVOC. – 2005. – №8. – P. 10-43.
- Lavallo V., Mafhouz J., Canac Y. et al. // J. Am. Chem. Soc. – 2004. – Vol. 126, №28. – P. 8670-8671.
- Menu M.J., Dartiguenave Y., Dartiguenave M. et al. // Phosphorus Sulfur & Silicon. – 1990. – Vol. 47, №3-4. – P. 327-334.
- Despagnet E., Gornitzka H., Rozhenko A.B. et al. // Angew. Chem. Int. Ed. Engl. – 2002. – Vol. 41, №15. – P. 2835-2837.
- Canac Y., Conejero S., Donnadieu B. et al. // J. Am. Chem. Soc. – 2005. – Vol. 127, №20. – P. 7312-7313.
- Knishevitsky A.V., Korotkikh N.I., Cowley A.H. et al. // ARKIVOC. – 2012. – №2. – P. 60-73.
- Alder R.W. / In: Carbene Chemistry. From Fleeting Intermediates to Powerful Reagents. G. Bertrand (Ed.). – New York: Fontis Media, 2002. – P. 157.
- Alcarazo M., Roseblade S.J., Alonso E. et al. // J. Am. Chem. Soc. – 2004. – Vol. 126, №41. – P. 13242-13243.
- Короткіх М.І., Швайка О.П. Карбеновий та карбенокомплексний каталіз органічних реакцій. – Донецьк: ДонНУ, 2013. – 372 с.
- Варфоломеев С.Д., Ефременко Е.Н., Крылова Л.П. // Усп. химии. – 2010. – T. 79, №6. – C. 544-564.
- Dove A.P., Pratt R.C., Lohmeijer B.G.G. et al. // In: N-Heterocyclic Carbenes in Synthesis, Nolan S.P. (Ed.). – Weinheim; Wiley-VCH Verlag GmbH &Co, KGaA, 2006. – P. 275.
- Nyce G.W., Lamboy J.A., Connor E.F. et al. // Org. Lett. – 2002. – Vol. 4, №21. – P. 3587-3590.
- Connor E.F., Nyce G.W., Myers M. et al. // J. Am. Chem. Soc. – 2002. – Vol. 124, №6. – P. 914-915.
- Movassaghi M., Schmidt M.A. // Org. Lett. – 2005. – Vol. 7, №12. – P. 2453-2456.
- Kühl O. Functionalized N-Heterocyclic Carbene Complexes. – Weinheim: Wiley-VCH, 2010. – P. 13.
- Марічев К.О., Короткіх М.І., Кисельов А.В. та ін. // Доп. НАН України. – 2011. – №7. – C. 133-137.
- Короткіх М.І., Марічев К.О., Кнішевицький А.В. та ін. – Пат. 68789 Україна МПК C 07 D, C 07 C. – 2012. – Бюл. №7.
- Marichev K.A., Korotkikh N.I., Kiselyov A.V. et al. // International Congress on Organic Chemistry dedicated to the 150-th anniversary of the Butlerov’s Theory of Chemical Structure of Organic Compounds. – Kazan, Russia, 2011. – P. 209.
- Ma Y., Wei S., Lan J. et al. // J. Org. Chem. – 2008. – Vol. 73, №21. – P. 8256-8264.
- Kano T., Sasaki K., Maruoka K. // Org. Lett. – 2005. – Vol. 7, №7. – P. 1347-1349.
- Breslow R. // J. Am. Chem. Soc. – 1957 – Vol. 79, №7. – P. 1762-1763.
- Breslow R. // J. Am. Chem. Soc. – 1958. – Vol. 80, №14. – P. 3719-3726.
- Enders D., Niemeier O., Henseler A. // Chem. Rev. – 2007. – Vol. 107, №12. – P. 5606-5655.
- Hashmi A.S.K., Wolfe M., Teles J.H., Frey W. // Synlett. – 2007. – №11. – P. 1747-1752.
- Маричев К.А., Коротких Н.И., Киселев А.В. и др. // Вторая Всерос. науч. конф. с междунар. участием «Успехи синтеза и комплексообразования». – М.: РУДН, 2012, 23-27 апреля. – C. 136.
- Cookson R., Lane R.M. // J. Chem. Soc., Chem. Commun. – 1976. – №127. – Р. 804.
- Takikawa H., Hachisu H., Bode J.W., Suzuki K. // Angew. Chem., Int. Ed. – 2006. – Vol. 45, №21. – P. 3492-3494.
- Teles J.H., Breuer K., Enders D., Gielen H. // Synth. Commun. – 1999. – Vol. 29, №1. – P. 1-9.
- Enders D., Grossmann A., Fronert J., Raabe G. // Chem. Commun. – 2010. – №46. – P. 6282-6284.
- Sheehan J.C., Hara T. // J. Org. Chem. – 1974. – Vol. 39, №9. – P. 1196-1199.
- Коротких М.И., Саберов В.Ш., Глиняная Н.В. и др. // ХГС. – 2013. – №1. – C. 25-46.
- Teles J.H., Melder J.-P., Ebel K. et al. // Helv. Chim. Acta. – 1996. – Vol. 79, №1. – P. 61-83.
- Matsumoto T., Yamamoto H., Inoue S. // J. Am. Chem. Soc. – 1984. – Vol. 106, №17. – P. 4829-4832.
- Stetter H. // Angew. Chem. Int. Ed. Engl. – 1976. – Vol. 15, №11. – P. 639-647.
- Pesch J., Harms K., Bach T. // Eur. J. Org. Chem. – 2004. – №9. – P. 2025-2035.
- Kerr M.S., de Alaniz J.R., Rovis T. // J. Am. Chem. Soc. – 2002. – Vol. 124, №35. – P. 10298-10299.
- Kerr M.S., Rovis T. // Synlett. – 2003. – №12. – P. 1934-1936.
- Kerr M.S., Rovis T. // J. Am. Chem. Soc. – 2004. – Vol. 126, №29. – P. 8876-8877.
- Read de Alaniz J., Rovis T. // J. Am. Chem. Soc. – 2005. – Vol. 127, №17. – P. 6284-6289.
- Enders D., Breuer K., Teles J.H. // Helv. Chim. Acta. – 1996. – Vol. 79. – P. 1217-1221.
- Nakamura T., Hara O., Tamura T. et al. // Synlett. – 2005. – №1. – P. 155-157.
- Ciganek E. // Synthesis. – 1995. – №10. – P. 1311-1314.
- Song J.J., Tan Z., Reeves J.T. et al. // Org. Lett. – 2005. – Vol. 7, №11. – P. 2193-2196.
- Miyashita A., Suzuki Y., Iwamoto K. et al. // Heterocycles. – 1998. – Vol. 49, №3. – P. 405-407.
- Miyashita A., Obae K., Suzuki Y. et al. // Heterocycles. – 1997. – Vol. 45, №11. – P. 2159-2173.
- Suzuki Y., Toyota T., Imada F. et al. // Chem. Commun. – 2003. – №12. – P. 1314-1315.
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