Catalytic oxidative carboncarbon bond cleavage of ketones with dioxygen: assessment of some metal complexes. Some alternatives for preparing α, ω-dicarboxylic acids

Morette A., Gaudefroy G., Bull. Soc. Chim. Fr. (1954) 956–964. Littler J.S., Waters W.A., J. Chem. Soc. (1959) 1299–1305. Littler J.S., Waters W.A., J. Chem. Soc. (1959) 3014–3019. Brégeault, 1988, C. R. Acad. Sci. Paris, série II, 307, 2011 Sheldon R.A., Kochi J.K.(Eds.), Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981, pp. 363–368. Larock R.C. (Ed.), Comprehensive Organic Transformations, Wiley-VCH, New York, 1999, pp. 1663–1664. Olah G.A., Ramos M.T., Wang Q., Prakash G.K.S., Synlett (1991) 41–43. Auburn, 1985, J. Am. Chem. Soc., 107, 2033, 10.1021/ja00293a038 Dai, 1993, J. Org. Chem., 58, 1900, 10.1021/jo00059a049 Porter, 1991, J. Am. Chem. Soc., 113, 1791, 10.1021/ja00005a051 Moriarty R.M., Prakash I., Penmasta R., J. Chem. Soc. Chem. Comm. (1987) 202–203. Kathó A., Beck M.T., Synlett (1992) 165–166. Oare, 1990, J. Org. Chem., 55, 157, 10.1021/jo00288a028 Reeves, 1988, Org. Syn. Coll., 6, 625 Davis D.D., Kemp D.R. in: Kroschwitz J.I., Howe–Grant M. (Eds.), Kirk Othmer Encyclopedia of Chemical Technology, vol.1, 4th Ed., Wiley, New York, 1991, pp.466–493. Holleman, 1905, Rec. Trav. Chim. Pays-Bas, 24, 19, 10.1002/recl.19050240104 Osowska-Pacewicka, 1988, J. Org. Chem., 53, 808, 10.1021/jo00239a023 Mercer, 1977, J. Am. Chem. Soc., 99, 6551, 10.1021/ja00462a014 Atlamsani, 1991, New J. Chem., 15, 671 Atlamsani A., Brégeault J.-M., Synthesis (1993) 79–81. Kozhevnikov, 1998, Chem. Rev., 98, 171, 10.1021/cr960400y Smidt, 1962, Angew. Chem. Int. Ed. Engl., 1, 80, 10.1002/anie.196200801 Kozhevnikov, 1982, Russ. Chem. Rev., 51, 1075, 10.1070/RC1982v051n11ABEH002941 Kozhevnikov, 1983, Appl. Catal., 5, 135, 10.1016/0166-9834(83)80128-6 Kozhevnikov, 1987, Uspeckni Khimii, 56, 1417 Zhizhina, 1986, React. Kinet. Catal. Lett., 31, 113, 10.1007/BF02062520 El Ali, 1987, J. Organomet. Chem., 327, C9, 10.1016/0022-328X(87)80237-1 Brégeault J.-M., El Ali B., Mercier J., Martin J., Martin C., Mohammedi O., in: New Developments in Selective Oxidation, Centi G., Trifirò F. (Eds.), University of Bologna, Italy, 1989, paper D7. Brégeault J.-M., Catalyse homogène par les complexes des métaux de transition, Masson, Paris, 1992, pp. 49–56. Grate J.H., Hamm D.R., Klingman K., Saxton R., Downey S., Catalytica, International Patent WO 91/13854, 1991. Grate J.H., Hamm D.R., Mahajan S., in: Kosak J.R., Johnson Th. A. (Eds.), Catalysis of Organic Reactions, Marcel Dekker, New York, 1994, p. 213. Mohammedi O., PhD thesis, University Pierre-et-Marie-Curie, Paris-6, 1987. Mohammedi, 1998, J. Soc. Alger. Chim., 8, 101 Faraj, 1985, J. Mol. Catal., 31, 57, 10.1016/0304-5102(85)85073-2 Martin, 1986, J. Mol. Catal., 37, 201, 10.1016/0304-5102(86)85009-X Derdar, 1988, J. Organomet. Chem., 338, C21, 10.1016/0022-328X(88)80515-1 The oxidative cleavage of organic compounds by bismuth complexes was reported recently, see: Zevaco T., Duñach E., Postel M., Tetrahedron Lett. 34 (1993) 2601–2604. Le Boisselier, 1994, J. Organometal. Chem., 482, 119, 10.1016/0022-328X(94)88192-8 Le Boisselier, 1995, Tetrahedron Lett., 51, 4991, 10.1016/0040-4020(95)98696-F Vasilevskis J., De Deken J., Saxton R., Wentrcek P.R., Fellmann J.D., Kipnis L.S., Catalytica Assoc., W.O. Patent 87/01615, 1987. Brégeault J.-M., El Ali B., Martin J., Patents FR 88–11075; EP 0355075 B1; US 4 983 767; CA 1 322 762; JP 1 8932–55, 1988. Ito, 1983, J. Org. Chem., 48, 1133, 10.1021/jo00155a051 Sagami Chem. Res. Centre, Japanese Patent J57181039–A and J89018889–B. El Ali, 1989, New J. Chem., 13, 173 El Ali B., Brégeault J.-M., Mercier J., Martin J., Martin C., Convert O., J. Chem. Soc. Chem. Comm. (1989) 825–826. Brégeault, 1990, Stud. Surf. Sci. Catal., 55, 205, 10.1016/S0167-2991(08)60150-0 Atlamsani, 1993, J. Org. Chem., 58, 5663, 10.1021/jo00073a026 Atlamsani, 1995, J. Chim. Phys., 92, 1344, 10.1051/jcp/1995921344 Hirao, 1989, Bull. Chem. Soc. Jpn, 62, 2399, 10.1246/bcsj.62.2399 Masilamani D., Manahan E.H., Allied Corp., US Patent 4 5103 21 A, 1985; C.A. 103:21899. He, 1999, Bull. Chem. Soc. Jpn, 72, 2515, 10.1246/bcsj.72.2515 Wrobel, 1990, J. Org. Chem., 55, 2694, 10.1021/jo00296a028 DiGrandi, 1993, J. Org. Chem., 58, 7728, 10.1021/jo00079a017 Nwaukwa, 1982, Tetrahedron Lett., 23, 3135, 10.1016/S0040-4039(00)88578-0 Kirihara, 1998, J. Chem. Soc. Perkin Trans., I, 7, 10.1039/a706859j Sigel H. (Ed.), Metal ions in biological systems, vol. 12, Marcel Dekker, New York, 1989. Walden P., Bull. Acad. Imper. Sci. Saint-Petersburg (1914) 1800. Sugden S., Wilkins H., J. Chem. Soc. (1929) 1291. Brégeault J.-M. et al., unpublished results. Cossy, 1994, Tetrahedron Lett., 35, 6089, 10.1016/0040-4039(94)88083-2 Launay F., Atlamsani A., Brégeault J.-M., to be submitted. Cherches K.A., Stanovaya S.S., Kostygov A.S., Zinder V.I., Patents SU 407876 731210, 1973. Davis D.D., in: Ullmann's Encyclopedia of Industrial Chemistry, vol. Al, VCH, Weinheim, 1985, pp. 269–278. Castellan, 1991, Catal. Today, 9, 237, 10.1016/0920-5861(91)80049-F Schuchardt, 1993, Synlett, 10, 713, 10.1055/s-1993-22583 Lindsay Smith, 1985, J. Chem. Soc, Perkin Trans., II, 1677, 10.1039/p29850001677 Trogler, 1999, Coord. Chem. Rev., 187, 303, 10.1016/S0010-8545(98)00254-9 Zeng, 1997, Appl. Catal. B–Environ., 13, 113, 10.1016/S0926-3373(96)00096-3 Panov, 1992, Appl. Catal. A–Gen., 82, 31, 10.1016/0926-860X(92)80003-U Häfele, 1997, Appl. Catal. A–Gen., 150, 153, 10.1016/S0926-860X(96)00283-9 Druliner J.D., Greller L.D., Roelofs M.G., Wasserman E., in: Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Moser W.R., Slocum D.W. (Eds.), American Chem. Soc., Washington, 1992, p. 6. Tsigdinos, 1968, Inorg. Chem., 7, 437, 10.1021/ic50061a009 Tsigdinos, 1978, Top. Curr. Chem., 76, 1, 10.1007/BFb0047026 Pettersson, 1994, Inorg. Chem., 33, 982, 10.1021/ic00083a023 Grate, 1996, J. Mol. Catal. A, 114, 93, 10.1016/S1381-1169(96)00307-X Brégeault J.-M., Laucher M., Costantini M., Enveloppe Soleau: L 91041 INPI. Costantini M., Krumenacker L., Rhône-Poulenc Chimie de Base, French Patent FR 83–3649 830; C.A. 102:25201. Franz G., Sheldon R.A., in: Ullmann's Encyclopedia of Industrial Chemistry, vol. A18, VCH, Weinheim, 1991, p. 268. Salles, 1994, Inorg. Chem., 33, 871, 10.1021/ic00083a008 Aubry, 1991, Inorg. Chem., 30, 4409, 10.1021/ic00023a024 Salles, 1993, New J. Chem., 17, 367 Salles, 1996, Bull. Soc. Chim. Fr., 133, 319 Butler, 1994, Chem. Rev., 94, 625, 10.1021/cr00027a004 Schwendt, 1995, Inorg. Chem., 34, 1964, 10.1021/ic00111a053 Schwendt, 1996, Polyhedron, 15, 4507, 10.1016/0277-5387(96)00185-4 Mimoun H., Sérée de Roch I., Sajus L., Bull. Soc. Chim. Fr. (1969) 1481–1492. Mimoun, 1970, Tetrahedron Lett., 26, 37, 10.1016/0040-4020(70)85005-0 Alonso, 1999, J. Solid State Chem., 148, 16, 10.1006/jssc.1999.8283 Bolm, 1999, Angew. Chem. Int. Ed. Engl., 38, 907, 10.1002/(SICI)1521-3773(19990401)38:7<907::AID-ANIE907>3.0.CO;2-# Draths, 1994, J. Am. Chem. Soc., 116, 399, 10.1021/ja00080a057 Frost J.W., Draths K.M., PCT Int. Appl. WO 9507996 Al, 1995; C.A.: 122:289072. Nagahara H., Konishi M., Japanese Patent 62-45541, 1987. Nagahara H., Konishi M., Japanese Patent 61-50930, 1986. Mitsui O., Fukuoka Y., Japanese Patent 59-184138 and 59-186929, 1984. Shimizu, 1996, J. Mol. Catal. A., 114, 217, 10.1016/S1381-1169(96)00320-2 Soncini P., Bonsignore S., European Patent Appl. EP 593 129, 1994; C.A.: 121:303538q. Iwahama, 1995, Tetrahedron Lett., 36, 1523, 10.1016/0040-4039(95)00075-N Sato, 1998, Science, 281, 1646, 10.1126/science.281.5383.1646 Noyori R., Sato K., Aoki M., JP 2000086574 A2, 2000; C.A.: 132:236807. Antonelli, 1998, J. Org. Chem., 63, 7190, 10.1021/jo980481t Knops-Gerrits, 1994, Stud. Surf. Sci. Catal., 84, 1411, 10.1016/S0167-2991(08)63682-4 ‘In our hands’, under the standard conditions of olefin epoxidation [see 79, 80, 82] –onium ions: n–Bu4N+, n–Hex4N+, Arquad 2HT®, Aliquat®, etc. are partially oxidized on C–1. Deng Y., Ma Z., Wang K., Chen J., Green Chemistry 1 (1999) 275–276. Goor G., in: Strukul G. (Ed.), Catalytic Oxidations with Hydrogen Peroxide as Oxidant, Kluwer Academic Publishers, Dordrecht, 1992, pp. 13–44. Brégeault, 1989, C. R. Acad. Sci. Paris, série II, 309, 459 Wilhoit E.D., Du Pont, US Patent 5 236 561, 1993. Kollar J., Redox Technologies, US Patent 5 321 157, 1994. Tanaka, 1974, Chem. Technol., 4, 555 Nakano T., Ishii Y., Daicel Chemical Industries Ltd, European Patent Appl. EP 858, 835, 1998; C.A.: 129:190734v. Ishii Y., Nakano T., Daicel Chemical Industries Ltd, PCT Int. Appl. WO 9728897, 1997; C.A.: 127:206051. Ishii, 1997, J. Mol. Catal. A., 117, 123, 10.1016/S1381-1169(96)00265-8 Ishii, 1999, Catalysis Surv. Jpn, 3, 27, 10.1023/A:1019059315516 Ishii, 1998, Org. Process. Res. Dev., 2, 255, 10.1021/op980016y Costantini M., Fache E., Laurent G., Rhône-Poulenc Fiber and Resin Intermediates, PCT Int. Appl. WO 96 31 455, 1996; C.A.: 125:328146f. Sankar, 1998, Catal. Lett., 55, 15, 10.1023/A:1019093703743 Dugal, 2000, Angew. Chem. Int. Ed. Engl., 39, 2310, 10.1002/1521-3773(20000703)39:13<2310::AID-ANIE2310>3.0.CO;2-G Belkhir, 1998, J. Chem. Soc. Faraday Trans., 94, 1761, 10.1039/a801245h Belkhir, 1997, Stud. Surf. Sci. Catal., 110, 577, 10.1016/S0167-2991(97)81019-1 Raja, 2000, Angew. Chem. Int. Ed. Engl., 39, 2313, 10.1002/1521-3773(20000703)39:13<2313::AID-ANIE2313>3.0.CO;2-Z Balkus, 1996, App. Catal. A–Gen., 143, 159, 10.1016/0926-860X(96)00078-6 Thibault-Starzyk, 1994, Stud. Surf. Sci. Catal., 84, 1419, 10.1016/S0167-2991(08)63683-6 Raja, 1997, Catal. Lett., 48, 1, 10.1023/A:1019054415786 Raja R., Ratnasamy P., EP 0784045, 1998, and US Patent 5767320, 1998. Haber, 1934, Proc. R. Soc. London A, 147, 332, 10.1098/rspa.1934.0221 Davies L., McMorn P., Bethell D., Bulman Page P.C., King F., Hancock F.E., Hutchings G.J., Chem. Commun. (2000) 1807–1808. Beck, 1992, J. Am. Chem. Soc., 114, 10834, 10.1021/ja00053a020 Hayashi T., Kishida A., Mizuno N., Chem. Commun. (2000) 381–382. Brunner H., Lane S., Murphree B., US Patent 5710325, 1998. Horiguchi S., Gomi K., Takeda K., JP 01023895 A2 890126, 1995. Burke P.M., European Patent Appl. EP 395038, 1990; C.A.: 114:142671r. Brivet J., Henriet E.B., Patois C., Perron R., PCT Int. Appl. WO 9747 580, 1997; C.A.: 128:61905g. Denis P., Patois C., Perron R., European Patent Appl., EP 612711, 1994; C.A.: 122:30961u. Launay, 1998, Tetrahedron Lett., 39, 1353, 10.1016/S0040-4039(97)10834-6 Barton, 1998, Tetrahedron Lett., 54, 5805, 10.1016/S0040-4020(98)00155-0