Abstract
Synthetic and mechanistic aspects of the developed approach to the activation of aromatic nitriles are considered. The approach is based on the transformation of aromatic nitriles into stable anionic reduced forms. The latter, as shown for the reactions with alkyl halides and cyanoarenes, are promising reactants for the reactions with carbon-centered electrophiles.
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P. H. Reiger, I. Bernal, W. H. Reinmuth, G. K. Fraenkel, J. Am. Chem. Soc., 1963, 85, 683.
K. Kano, K. Mori, B. Uno, M. Goto, T. Kubota, J. Am. Chem. Soc., 1990, 112, 8645.
M. Sertel, A. Yildiz, R. Gambert, H. Baumgartel, Electrochim. Acta, 1986, 31, 1287.
A. Genaro, F. Maran, A. Maye, E. Vianello, J. Electroanal. Chem., 1985, 185, 353.
A. Genaro, A. Maye, F. Maran, E. Vianello, Electrochim. Acta, 1988, 33, 167.
I. N. Juchnovsky, I. B. Binev, J. Kanety, J. Com. Dep. Chem., Bulg. Acad. Sci., 1977, 10, 554.
K. A. Brown-Wensley, S. L. Mattes, S. Farid, J. Am. Chem. Soc., 1978, 100, 4162; F. D. Lewis, J. R. Petisce, Tetrahedron, 1987, 42, 6207.
H. S. Sorensen, K. Daasbjerg, Acta Chem. Scand., 1998, 52, 51.
D. Occhialini, J. S. Kristensen, K. Daasbjerg, H. Lund, Acta Chem. Scand., 1992, 46, 474.
P. Furderer, F. Gerson, Helv. Chim. Acta, 1976, 50, 2492.
A. Yildiz, H. Baumgartel, Ber. Bunsen-Ges. Phys. Chem., 1977, 81, 1177.
I. I. Bil’kis, T. A. Vaganova, A. Yu. Denisov, V. D. Shteingarts, Zh. Org. Khim., 1987, 23, 2062 [J. Org. Chem. USSR, 1987, 23, 1823 (Engl. Transl.)].
I. I. Bil’kis, T. A. Vaganova, V. I. Bobyleva, V. D. Shteingarts, Zh. Org. Khim., 1991, 27, 48 [J. Org. Chem. USSR, 1991, 27, 41 (Engl. Transl.)].
I. I. Bil’kis, T. A. Vaganova, V. D. Shteingarts, Zh. Org. Khim., 1990, 26, 2044 [J. Org. Chem. USSR, 1990, 26, 1765 (Engl. Transl.)].
I. I. Bil’kis, T. A. Vaganova, S. I. Pimnev, V. D. Shteingarts, Zh. Org. Khim., 1991, 27, 1722 [J. Org. Chem. USSR, 1991, 27, 1513 (Engl. Transl.)].
E. V. Panteleeva, I. I. Bil’kis, V. D. Shteingarts, Zh. Org. Khim., 1998, 34, 1702 [Russ. J. Org. Chem., 1998, 34, 1632 (Engl. Transl.)].
I. I. Bil’kis, E. V. Panteleeva, A. P. Tananakin, V. D. Shteingarts, Zh. Org. Khim., 1994, 30, 882 [Russ. J. Org. Chem., 1994, 30, 941 (Engl. Transl.)].
T. A. Vaganova, E. V. Starokon’, V. D. Shteingarts, Zh. Org. Khim., 2002, 38, 865 [Russ. J. Org. Chem., 2002, 38, 823 (Engl. Transl.)].
T. A. Vaganova, E. V. Starokon’, V. D. Shteingarts, Zh. Org. Khim., 2003, 39, 725 [Russ. J. Org. Chem., 2003, 39, 680 (Engl. Transl.)].
T. A. Vaganova, L. M. Pokrovskii, V. D. Shteingarts, Zh. Org. Khim., 2001, 37, 72 [Russ. J. Org. Chem., 2001, 37, 62 (Engl. Transl.)].
P. H. Reiger, G. K. Fraenkel, J. Chem. Phys., 1962, 37, 2795.
A. J. Birch, A. L. Hindle, L. Radom, J. Am. Chem. Soc., 1980, 102, 3370.
N. V. Vasilieva, I. G. Irtegova, T. A. Vaganova, V. D. Shteingarts, J. Phys. Org. Chem., 2008, 21, 73.
T. A. Vaganova, E. V. Panteleeva, A. P. Tananakin, V. D. Shteingarts, I. I. Bilkis, Tetrahedron, 1994, 50, 10011.
K. Nakanishi, K. Mizuno, Y. Otsuji, Bull. Chem. Soc. Jpn, 1993, 66, 2371.
V. F. Starichenko, N. V. Efremova, V. D. Shteingarts, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2170 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 1949 (Engl. Transl.)].
Ch. Amatore, C. Combelas, S. Robveille, J.-M. Saveant, A. Tiebault, J. Am. Chem. Soc., 1986, 108, 4754.
J.-M. Saveant, Acta Chem. Scand., 1988, 37B, 365.
E. V. Panteleeva, T. A. Vaganova, E. A. Luk’yanets, V. D. Shteingarts, Zh. Org. Khim., 2006, 42, 1301 [Russ. J. Org. Chem., 2006, 42, 1280 (Engl. Transl.)].
I. I. Bilkis, T. A. Vaganova, E. V. Panteleeva, A. P. Tananakin, G. E. Salnikov, V. I. Mamatyuk, V. D. Shteingarts, J. Phys. Org. Chem., 1994, 7, 153.
T. A. Vaganova, P. S. Yuferov, L. I. Goryunov, E. V. Panteleeva, G. E. Sal’nikov, L. N. Shchegoleva, V. I. Mamatyuk, V. D. Shteingarts, Izv. Akad. Nauk, Ser. Khim., 2006, 940 [Russ. Chem. Bull., Int. Ed., 2006, 55, 976].
I. I. Bil’kis, E. V. Panteleeva, A. P. Tananakin, V. D. Shteingarts, Zh. Org. Khim., 1997, 33, 711 [Russ. J. Org. Chem., 1997, 33, 652 (Engl. Transl.)].
E. V. Panteleeva, G. Haufe, V. D. Shteingarts, Synlett, 2007, 1616.
T. A. Vaganova, I. I. Bil’kis, V. D. Shteingarts, Zh. Org. Khim., 1986, 22, 2239 [J. Org. Chem. USSR, 1986, 22, 2011 (Engl. Transl.)].
I. I. Bil’kis, T. A. Vaganova, V. D. Shteingarts, Zh. Org. Khim., 1994, 30, 892 [Russ. J. Org. Chem., 1994, 30, 951 (Engl. Transl.)].
A. G. Schultz, M. Macielag, J. Org. Chem., 1986, 51, 4983.
T. A. Vaganova, E. V. Panteleeva, P. S. Yuferov, Yu. V. Rebitva, V. D. Shteingarts, Izv. Akad. Nauk, Ser. Khim., 2006, 945 [Russ. Chem. Bull., Int. Ed., 2006, 55, 981].
J. G. Smith, D. C. Irwin, J. Am. Chem. Soc., 1980, 102, 2757; I. I. Bilkis, in Supplement B: The Chemistry of Acid Derivatives, Ed. S. Patai, Wiley, New York, 1992, 2, 1639.
I. I. Bilkis, B. A. Selivanov, V. D. Shteingarts, Res. Chem. Intermed., 1993, 9, 463.
N. L. Holy, Chem. Rev., 1974, 74, 243; S. Bank, J. F. Bank, in Organic Free Radicals, Ed. W. A. Pryor, Am. Chem. Soc., Washington, 1978, 343; I. I. Bil’kis, V. D. Shteingarts, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1987, 17, 105 [Izv. Sib. Otd. Akad. Nauk SSSR. Ser. Khim. Nauk, 1987, 17 (Engl. Transl.)]; J. F. Garst, C. D. Smith, J. Am. Chem. Soc., 1976, 98, 1520.
D. Occhialini, S. Pedersen, H. Lund, Acta Chem. Scand., 1992, 46, 715.
E. V. Panteleeva, T. A. Vaganova, V. D. Shteingarts, I. I. Bilkis, Tetrahedron Lett., 1995, 36, 8465.
T. A. Vaganova, V. D. Shteingarts, Zh. Org. Khim., 2004, 40, 781 [Russ. J. Org. Chem., 2004, 40, 747 (Engl. Transl.)].
J. Walton, Magn. Res. Chem., 1987, 25, 998.
J. Grimshaw, J. R. Langan, J. A. Salmon, J. Chem. Soc., Faraday Trans., 1994, 90, 75.
E. S. Lewis, J. Am. Chem. Soc., 1989, 111, 7576.
D. Lexa, J.-M. Saveant, K.-B. Su, D.-L. Wang, J. Am. Chem. Soc., 1988, 110, 7617.
M. Newcomb, Acta Chem. Scand., 1990, 44, 299.
M. Newcomb, A. G. Glenn, J. Am. Chem. Soc., 1989, 111, 275.
Y. Huang, D. D. M. Wayner, J. Am. Chem. Soc., 1994, 116, 2157.
A. Pross, Acc. Chem. Res., 1985, 18, 212; T. Lund, H. Lund, Acta Chem. Scand., Ser. B, 1986, 40, 471; H. Lund, K. Daasbjerg, T. Lund, D. Ochialini, S. U. Pedersen, Acta Chem. Scand., 1997, 51, 135.
L. Eberson, S. S. Shaik, J. Am. Chem. Soc., 1990, 112, 4484; S. Shaik, D. Danovich, G. N. Sastry, P. Y. Ayala, H. B. Schlegel, J. Am. Chem. Soc., 1997, 119, 9237; G. N. Sastry, S. Shaik, J. Am. Chem. Soc., 1995, 117, 3290.
P. D. Burrow, P. D. Modeli, A. Modeli, N. S. Chiu, K. D. Jordan, J. Chem. Phys., 1982, 77, 2699.
J.-M. Saveant, J. Am. Chem. Soc., 1992, 114, 10595.
E. V. Panteleeva, M. Yu. Luk’yanova, L. M. Pokrovskii, V. D. Shteingarts, Izv. Akad. Nauk, Ser. Khim., 2007, 1069 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1110].
V. Ganesan, S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc., 2003, 125, 2559.
R. E. Del Sesto, J. S. Miller, P. Lafuente, J. J. Novoa, Chem. Eur. J., 2002, 8, 4894.
J. K. Kochi, Angew. Chem., Int. Ed. Engl., 1988, 29, 1227.
J. K. Kochi, Acta Chem. Scand., 1990, 44, 409.
J. K. Kochi, Pure Appl. Chem., 1991, 63, 255.
E. Panteleeva, L. Shchegoleva, V. Vysotsky, L. Pokrovsky, V. Shteingarts, Eur. J. Org. Chem., 2005, 2558.
T. A. Vaganova, E. V. Panteleeva, V. D. Shteingarts, in Panorama sovremennoi khimii Rossii. Sovremennyi organicheskii sintez [Panorama of the Modern Chemistry in Russia. Modern Organic Synthesis], Khimiya, Moscow, 2003, 293 (in Russian).
Friedel-Crafts and Related Reactions, Ed. G. A. Olah, Wiley, New York, 1963–1964; G. A. Olah, R. Krishnamurti, G. K. Prakash, Comprehensive Organic Synthesis, Pergamon Press, New York, 1991, 3, 293; T. Miyai, Y. Onishi, A. Baba, Tetrahedron, 1999, 55, 1017; M. Mahindarante, K. Wimalasena, J. Org. Chem., 1998, 63, 2858.
M. Catellani, G. P. Chiusoli, J. Organomet. Chem., 1988, 346, 27; B. H. Lipshutz, P. A. Blomgren, S.-K. Kim, Tetrahedron Lett., 1999, 40, 197; T. Harada, M. Chiba, A. Oku, J. Org. Chem., 1999, 64, 8210.
PCT Int. Appl. WO 9749672; Chem. Abstrs, 1998, 128, 101906; E. Fattorusso, L. Minale, G. Sodano, J. Chem. Soc., Chem. Commun., 1970, 752; M. Rotem, S. Carmely, J. Kashman, J. Loya, Tetrahedron, 1983, 39, 667; J. Salaun, M. S. Baird, Curr. Med. Chem., 1995, 2, 511.
Author’s Certificate of the USSR 1705280; Byul. Izobret. [Invention Bulletin], 1992, 2, 99; Chem. Abstrs, 1992, 117, 89975.
Pat. DE2456077; Chem. Abstrs, 1976, 85, 114843n; Pat. Jpn Kokai 77 20, 985; Chem. Abstrs, 1977, 86, 198027f; R. Steinstraesser, Z. Naturforsch., Teil B, 1972, 27, 774; C. H. Tani, T. Veno, S. Naemura, I. T. Mimi, F. Ogawa, NEC Res. Dev., 1981, 61, 42; Pat. Jpn Kokai 74 34, 488; Chem. Abstrs, 1974, 81, 144290q; Pat. DE3002678; Chem. Abstrs, 1981, 94, P46976s.
Pat. US 3764621; Chem. Abstrs, 1974, 80, 14655f.
Pat. Braz. Pedido PI 78 00, 095; Chem. Abstrs, 1979, 90, 181580r.
Pat. PL 87873; Chem. Abstrs, 1978, 88, 153909v.
Pat. Jpn Kokai Tokkyo Koho JP 64 44, 906 [86 44, 926]; Chem. Abstrs, 1986, 105, 153671f.
R. Csusk, M. J. Schabel, Y. von Scholz, Tetrahedron: Asymmetry, 1996, 7, 3505; Y. Nishii, N. Maryjama, K. Wakasugi, U. Tanabe, Bioorg. Med. Chem., 2001, 11, 33; J. S. Kumar, S. Roy, A. Datta, Bioorg. Med. Chem., 1999, 9, 513; T. C. Rosen, S. Yoshida, K. L. Kirk, G. Haufe, ChemBioChem., 2004, 5, 1033.
Pat. JP 04061118; Chem. Abstrs, 1992, 117, 162143k.
J. N. Ashley, H. J. Barber, A. J. Ewins, G. Newberry, A. D. H. Self, J. Chem. Soc., 1942, 103.
D. J. Cram, H. Steinberg, J. Am. Chem. Soc., 1951, 73, 5691.
M. F. Semmelhack, P. M. Helquist, L. D. Jones, J. Am. Chem. Soc., 1971, 93, 5908.
J. Hassan, C. Gozzi, M. Lemarie, C. R. Acad. Sci., Ser. IIc: Chim., 2000, 3, 517.
A. Inorue, K. Katagava, H. Shinokubo, C. Oshima, Tetrahedron, 2000, 56, 9601.
Pat. JP 52068155 19770606; Chem. Abstrs, 1978, 87, 152280.
M. Hanack, H. Heckmann, R. Polley, in Houben-Weyl: Hetarenes V, Ed. E. Schaumann, Thieme, Stuttgart, 1998, E9d, 868; N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function, Cambridge University Press, Cambridge, 1998, 211; S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, E. A. Luk’yanets, Zh. Obshch. Khim., 1971, 41, 2735 [J. Gen. Chem. USSR, 1971, 41 (Engl. Transl.)]; Phthalocyanines: Properties and Applications, Eds C. C. Leznoff, A. B. P. Lever, VCH, New York, 1989–1998, 1–4; M. Johannsen, K. A. Joergensen, J. Org. Chem., 1994, 59, 214; S. C. Sirlin, Pure Appl. Chem., 1989, 61, 1625; M. Emmelius, G. Pawlowski, H. W. Vollmann, Angew. Chem., 1989, 28, 1445.
E. A. Luk’yanets, Ros. Khim. Zh., 1998, 42, 9 [Mendeleev Chem. J., 1998, 42 (Engl. Transl.); Chem. Abstrs, 2000, 132, 32685]; R. Bonnett, Chem. Soc. Rev., 1995, 24, 19; M. E. Vol’pin, N. Yu. Krainova, I. V. Moskaleva, G. N. Novodarova, G. N. Vorozhtsov, M. G. Gal’pern, O. L. Kaliya, E. A. Luk’yanets, S. A. Mikhalenko, Izv. Akad. Nauk, Ser. Khim., 1996, 2105 [Russ. Chem. Bull., 1996, 45, 2000 (Engl. Transl.)]; B. del Rey, U. Keller, T. Torres, G. Rojo, F. Agullo-Lopez, S. Nonell, C. Marti, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc., 1998, 120, 12808.
W. O. Siegl, F. C. Ferris, P. A. Mucci, J. Org. Chem., 1977, 42, 3442; T. H. Fischer, A. W. Meierhoefer, J. Org. Chem., 1978, 43, 220.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 754–765, April, 2008.
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Vaganova, T.A., Panteleeva, E.V. & Shteingarts, V.D. Reductive activation of arenecarbonitriles for the reactions with some carbon-centered electrophiles: the reaction mechanisms and synthetic applications. Russ Chem Bull 57, 768–779 (2008). https://doi.org/10.1007/s11172-008-0116-6
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DOI: https://doi.org/10.1007/s11172-008-0116-6