Abstract
In recent decades, a large number of reports related to the synthesis of N-, O- and S-containing heterocycles have appeared owing to a wide variety of their biological activity. Traditional approaches require expensive or highly specialized equipment or would be of limited use to the synthetic organic chemist due to their highly inconvenient approaches. New strategies have been developed for the preparation of heterocycles in the last decades. Metal and non-metal catalysts are used in organic reactions with high activity. These synthetic strategies are becoming important and highly rewarding protocols in organic synthesis. In this review article, the synthesis of heterocycles is presented with the application of cobalt metal as a catalyst. It describes the formation of different sized heterocyclic rings containing different heteroatoms.
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References
A.T. Balaban, D.C. Oniciu, A.R. Katritzky, Chem. Rev. 104, 2777 (2004)
P. Majumdar, A. Pati, M. Patra, R.K. Behera, A.K. Behera, Chem. Rev. 114, 2942 (2014)
S. Madapa, Z. Tusi, S. Batra, Curr. Org. Chem. 12, 1116 (2008)
M.A.P. Martins, W. Cunico, C.M.P. Pereira, A.F.C. Flores, H.G. Bonacorso, N. Zanatta, Curr. Org. Synth. 1, 391 (2004)
N. Kaur, J. Heterocycl. Chem. 52, 953 (2015)
N. Kaur, Curr. Org. Synth. 14, 531 (2017)
N. Kaur, Curr. Org. Synth. 14, 972 (2017)
N. Kaur, Mini Rev. Org. Chem. 14, 3 (2017)
N. Kaur, Synth. React. Inorg. Met. Org. Nano-Met. Chem. 46, 983 (2016)
N. Kaur, Inorg. Nano-Met. Chem. 47, 163 (2017)
A. Domling, Chem. Rev. 106, 17 (2006)
N. Kaur, Synth. Commun. 48, 1551 (2018)
N. Kaur, Synth. Commun. 48, 1588 (2018)
N. Kaur, Synth. Commun. 48, 1715 (2018)
N. Kaur, Synth. Commun. 48, 2119 (2018)
N. Kaur, Synth. Commun. 48, 2715 (2018)
N. Kaur, Synth. Commun. 48, 2935 (2018)
N. Kaur, Synth. Commun. 48, 2815 (2018)
N. Kaur, Inorg. Chem. Commun. 99, 82 (2018)
R.V.A. Orru, M. de Greef, Synthesis 10, 1471 (2003)
N. Kaur, Synth. Commun. 49, 1205 (2019)
N. Kaur, Synth. Commun. 49, 879 (2019)
N. Kaur, Phosphorus, Sulfur, and Silicon and the Related. Elements 194, 165 (2019)
N. Kaur, Synth. Commun. 49, 1103 (2019)
N. Kaur, Synth. Commun. 49, 987 (2019)
N. Kaur, P. Bhardwaj, M. Devi, Y. Verma, P. Grewal, Synth. Commun. 49, 1345 (2019)
N. Kaur, Phosphorus, Sulfur, and Silicon and the Related. Elements 194, 186 (2019)
N. Kaur, Catal. Lett. 14, 1513 (2019)
N. Kaur, Inorg. Chem. Commun. 49, 86 (2014)
N. Kaur, D. Kishore, Synth. Commun. 44, 1173 (2014)
N. Kaur, D. Kishore, Synth. Commun. 44, 1019 (2014)
N. Kaur, Synth. Commun. 44, 3483 (2014)
N. Kaur, Synth. Commun. 44, 3509 (2014)
N. Kaur, Synth. Commun. 44, 3229 (2014)
N. Kaur, Synth. Commun. 48, 1235 (2018)
N. Kaur, Synth. Commun. 48, 1259 (2018)
N. Kaur, J. Sulfur Chem. 39, 544 (2018)
N. Kaur, D. Kishore, Catal. Surv. Asia 17, 20 (2013)
N. Kaur, D.J. Kishore, Iranian Chem. Soc. 10, 1193 (2013)
N. Kaur, D. Kishore, Synth. Commun. 44, 721 (2014)
N. Kaur, D. Kishore, J. Heterocycl. Chem. 51, E340 (2014)
N. Kaur, D. Kishore, J. Chem. Sci. 2014, 126 (1861)
N. Kaur, D. Kishore, Synth. Commun. 44, 2789 (2014)
N. Kaur, J. Iran. Chem. Soc. 12, 9 (2015)
N. Kaur, Synth. Commun. 45, 1269 (2015)
N. Kaur, Synth. Commun. 45, 1379 (2015)
N. Kaur, Synth. Commun. 44, 3201 (2014)
N. Kaur, Synth. Commun. 45, 1 (2015)
N. Kaur, Synth. Commun. 45, 35 (2015)
N. Kaur, Catal. Rev. 57, 478 (2015)
N. Kaur, D. Kishore, J. Chem. Sci. 125, 555 (2013)
N. Kaur, Syn. Commun. 45, 789 (2015)
N. Kaur, Synth. Commun. 45, 151 (2015)
N. Kaur, Synth. Commun. 45, 173 (2015)
N. Kaur, Synth. Commun. 45, 273 (2015)
N. Kaur, Synth. Commun. 45, 300 (2015)
N. Kaur, D. Kishore, Synth. Commun. 44, 1375 (2014)
N. Kaur, Curr. Org. Synth. 15, 940 (2018)
N. Kaur, Synth. Commun. 48, 2457 (2018)
Z. Ke, B. Yu, H. Wang, J. Xiang, J. Han, Y. Wu, Z. Liu, P. Yang, Z. Liu, Green Chem. 21, 1695 (2019)
N. Kaur, Syn. Commun. 45, 909 (2015)
N. Kaur, Synth. Commun. 45, 432 (2015)
N.J. Kaur, Iranian Chem. Soc. 11, 523 (2014)
N. Kaur, Synth. Commun. 45, 1145 (2015)
N. Kaur, Synth. Commun. 45, 1493 (2015)
N. Kaur, Synth. Commun. 45, 1599 (2015)
N. Kaur, Synth. Commun. 45, 1711 (2015)
N. Kaur, Synth. Commun. 49, 483 (2019)
N. Kaur, Synth. Commun. 49, 743 (2019)
N. Kaur, Synth. Commun. 49, 617 (2019)
S.M. Ujwaldev, N.A. Harry, M.A. Divakar, G. Anilkumar, Catal. Sci. Technol. 8, 5983 (2018)
K. Pal, O.B. Hemming, B.M. Day, T. Pugh, D.J. Evans, R.A. Layfield, Angew. Chem. Int. Ed. 55, 1690 (2016)
N.T. Patil, Y. Yamamoto, Chem. Rev. 108, 3395 (2008)
N. Kaur, Syn. Commun. 45, 403 (2015)
N. Kaur, Synth. Commun. 45, 539 (2015)
N. Kaur, D. Kishore, Synth. Commun. 44, 2577 (2014)
N. Kaur, D. Kishore, Synth. Commun. 44, 2615 (2014)
N. Kaur, D. Kishore, Synth. Commun. 44, 2739 (2014)
N. Kaur, Curr. Organocatal. 4, 122 (2017)
Y. Li, M. Wang, W. Fan, F. Qian, G. Li, H. Lu, J. Org. Chem. 81, 11743 (2016)
S.M. Ujwaldev, S. Saranya, N.A. Harry, G. Anilkumar, Monatshefte für Chem. Chem. Monthly 150, 339 (2019)
D. Alberico, M.E. Scott, M. Lautens, Chem. Rev. 107, 174 (2007)
B. Barré, L. Gonnard, A. Guérinot, J. Cossy, Molecules 23, 1449 (2018)
A.R. Dick, M.S. Sanford, Tetrahedron 62, 2439 (2006)
N. Kaur, Catal. Rev. 57, 1 (2015)
N. Kaur, D. Kishore, Synth. Commun. 44, 3082 (2014)
N. Kaur, D. Kishore, Synth. Commun. 44, 3047 (2014)
I. Nakamura, Y. Yamamoto, Chem. Rev. 104, 2127 (2004)
V. Snieckus, J.M. Curto, Synfacts 15, 0354 (2019)
S. Zhou, M. Wang, L. Wang, K. Chen, J. Wang, C. Song, J. Zhu, Org. Lett. 18, 5632 (2016)
G. Zeni, R.C. Larock, Chem. Rev. 106, 4644 (2006)
J.R. Hummel, J.A. Ellman, J. Am. Chem. Soc. 137, 490 (2015)
Dzhemilev, U.M. Selimov, F.A., Tolstikov G. A. ARKIVOC, 2001, (ix), 85
Z. Li, C. He, Eur. J. Org. Chem. 19, 4313 (2006)
H. Ohmiya, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2006, 128 (1886)
H. Ohmiya, K. Wakabayashi, H. Yorimitsu, K. Oshima, Tetrahedron 62, 2207 (2006)
H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 8, 3093 (2006)
H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 9, 1565 (2007)
H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Tetrahedron 63, 8609 (2007)
S. Diez-Gonzalez, N. Marion, S.P. Nolan, Chem. Rev. 109, 3612 (2009)
D. Roberto, H. Alper, J. Am. Chem. Soc. 111, 7539 (1989)
K. Khumtaveeporn, H. Alper, Acc. Chem. Res. 28, 414 (1995)
J. Jacob, C.K. Cavalier, W.D. Jones, S.A. Godleski, R.R.J. Valente, Mol. Catal. A. 183, 565 (2002)
M. Sato, Y. Gunji, T. Ikeno, T. Yamada, Synthesis 9, 1434 (2004)
T. Niwa, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 46, 2643 (2007)
P. Caramella, K.N. Houk, J. Am. Chem. Soc. 98, 6397 (1976)
R. Sustmann, Pure Appl. Chem. 40, 569 (1974)
Park, K. H.; Choi, S. Y.; Kim, S. Y.; Chung, Y. K. Synlett, 2006, 527
K.M. Brummond, J.L. Kent, Tetrahedron 56, 3263 (2000)
B.R. Galan, T. Rovis, Angew. Chem. Int. Ed. 48, 2830 (2009)
N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, M. Malacria, Org. React. 68, 1 (2007)
B. Heller, M. Hapke, Chem. Soc. Rev. 36, 1085 (2007)
P. Hong, H. Yamazaki, Synthesis 1, 50 (1977)
H. Hoberg, B.W. Oster, Synthesis 4, 324 (1982)
H. Hoberg, B.W. Oster, J. Organomet. Chem. 234, C35 (1982)
H. Hoberg, B.W. Oster, J. Organomet. Chem. 252, 359 (1983)
R.A. Earl, K.P.C. Vollhardt, J. Am. Chem. Soc. 105, 6991 (1983)
R.A. Earl, K.P.C. Vollhardt, J. Org. Chem. 49, 4786 (1984)
H.A. Duong, M.J. Cross, J. Louie, J. Am. Chem. Soc. 126, 11438 (2004)
Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 124, 5059 (2005)
K. Tanaka, Y. Takahashi, T. Suda, M. Hirano, Synlett 11, 1724 (2008)
K. Tanaka, A. Wada, K. Nogushi, Org. Lett. 7, 4737 (2005)
R.K. Friedman, K.M. Oberg, D.M. Dalton, T. Rovis, Pure Appl. Chem. 82, 1353 (2010)
S.R. Park, N.J. Findlay, J. Garnier, S. Zhou, M.D. Spicer, J.A. Murphy, Tetrahedron 65, 10756 (2009)
S. Nag, S. Batra, Tetrahedron 67, 8959 (2011)
W. Affo, H. Ohmiya, T. Fujioka, Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, Y. Imamura, T. Mizuta, K. Miyoshi, J. Am. Chem. Soc. 128, 8068 (2006)
A. Geny, S. Gaudrel, F. Slowinski, M. Amatore, G. Chouraqui, M. Malacria, C. Aubert, V. Gandon, Adv. Synth. Catal. 351, 271 (2009)
N. Kumagai, G. Muncipinto, S.L. Schreiber, Angew. Chem. Int. Ed. 45, 3635 (2006)
Hong, S. H.; Kim, J. W.; Choi, D. S.; Chung, Y. K.; Lee, S.-G. Chem. Commun. 1999, 2099
S.U. Son, D.S. Choi, Y.K. Chung, S.-G. Lee, Org. Lett. 2, 2097 (2000)
J.-M. Weibel, A. Blanc, P. Pale, Chem. Rev. 108, 3149 (2008)
Milbank, J. B. J.; Stevenson, R. J.; Ware, D. C.; Chang, J. Y. C.; Tercel, M.; Ahn, G.- O.; Wilson, W. R.; Denny, W. A. J. Med. Chem. 2009, 52, 6822
A.T. Khan, T. Parvin, Cheminform 40, 2339 (2009)
Alper, H.; Currie, J. K.; Abbayes, H. J. Chem. Soc. Chem. Comun. 1978, 311
A. Bermejo, B. Figadere, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes, Nat. Prod. Rep. 22, 269 (2005)
J.-C. Harmange, Figadere B. Tetrahedron Asymmetry 4, 1711 (1993)
Z. Chena, S. Subhash, Tetrahedron 64, 1603 (2008)
Dzhemilev, U.M., Selimov, F.A., Khafizov, V. R. Izv. AN SSSR, Ser.Khim. 1986, 1628
P. Turek, M. Kotora, M. Hocek, I. Cisarova, Tetrahedron Lett. 44, 785 (2003)
P. Turek, M. Kotora, I. Tislerova, M. Hocek, I. Votruba, I. Cisarova, J. Org. Chem. 69, 9224 (2004)
H.-W. Fruhauf, Chem. Rev. 97, 523 (1997)
O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. 37, 911 (1998)
Y.K. Chung, Coord. Chem. Rev. 188, 297 (1999)
S.-W. Kim, S.U. Son, S.I. Lee, T. Hyeon, Y.K. Chung, J. Am. Chem. Soc. 122, 1550 (2000)
A.C. Comely, S.E. Gibson, N.J. Hales, Chem. Commun. 4, 305 (2000)
M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. Int. Ed. 39, 631 (2000)
B.L. Pagenkopf, D.B. Belanger, D.J.R. O’Mahony, T. Livinghouse, Synthesis 7, 1009 (2000)
M.E. Krafft, L.V.R. Bonaga, Angew. Chem. Int. Ed. 39, 3676 (2000)
S.U. Son, S.I. Lee, Y.K. Chung, Angew. Chem. Int. Ed. 39, 4158 (2000)
M.E. Krafft, L.V.R. Bonaga, C. Hirosawa, J. Org. Chem. 66, 3004 (2001)
S.-W. Kim, S.U. Son, S.S. Lee, T. Hyeon, Y.K. Chung, Chem. Commun. 21, 2212 (2001)
A.C. Comely, S.E. Gibson, A. Stevenazzi, N.J. Hales, Tetrahedron Lett. 42, 1183 (2001)
T. Shibata, N. Toshida, K. Takagi, Org. Lett. 4, 1619 (2002)
S.E. Gibson, C. Johnstone, A. Stevenazzi, Tetrahedron 58, 4937 (2002)
T. Shibata, N. Toshida, K. Takagi, J. Org. Chem. 67, 7446 (2002)
M. Ishizaki, H. Satoh, O. Hoshino, Chem. Lett. 31, 1040 (2002)
B. Jiang, M. Xu, Org. Lett. 4, 4077 (2002)
K.H. Park, S.U. Son, Y.K. Chung, Chem. Commun. 2003, 15 (1898)
N. Saino, D. Kogure, S. Okamoto, Org. Lett. 7, 3065 (2005)
G. Cahiez, A. Moyeux, Chem. Rev. 110, 1435 (2010)
G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, Org. Lett. 11, 277 (2009)
M. Amatore, C. Gosmini, Chem. Commun. 40, 5019 (2008)
H. Yorimitsu, K. Oshima, Pure Appl. Chem. 78, 441 (2006)
H. Someya, A. Kondoh, A. Sato, H. Ohmiya, H. Yorimitsu, K. Oshima, Synlett 18, 3061 (2006)
H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 10, 5640 (2004)
Tsuji, T., Yorimitsu, H., Oshima, K. Angew. Chem. Int. Ed. 2002, 114, 4311; Angew. Chem. Int. Ed. 2002, 41, 4137
K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 123, 5374 (2001)
G. Li, D.C. Xiong, X.S. Ye, Synlett 16, 2410 (2011)
H. Gong, M.R. Gagn, J. Am. Chem. Soc. 130, 12177 (2008)
Miquel, N., Doisneau, G., Beau, J.M. Angew. Chem. Int. Ed. 2000, 112, 4277; Angew. Chem. Int. Ed. 2000, 39, 4111
Korth, H.G., Dupuis, J., Giese, B. J. Chem. Soc. Perkin Trans. 2 1986, 9, 1453
J. Dupuis, B. Giese, J. Am. Chem. Soc. 107, 4332 (1985)
Dupuis, J., Giese, B., Egge, D.R., Fischer, H., Korth, H.G., Sustmann, R. Angew. Chem. Int. Ed. 1984, 96, 887; Angew. Chem. Int. Ed. 1984, 23, 896
Giese, B., Dupuis, J. Angew. Chem. Int. Ed. 1983, 95, 633; Angew. Chem. Int. Ed. 1983, 22, 622
R.M. Adlington, J.E. Baldwin, A. Basak, R.P. Kozyrod, J. Chem. Soc., Chem. Commun. 17, 944 (1983)
J. Zheng, S. Vedachalam, S. Xiang, X.W. Liu, Org. Lett. 13, 42 (2011)
Andrews, R.S., Becker, J.J., Gagn, M. R. Angew. Chem. Int. Ed. 2010, 122, 7432; Angew. Chem. Int. Ed. 2010, 49, 7274
H. Gong, R.S. Andrews, J.L. Zuccarello, S.J. Lee, M.R. Gagn, Org. Lett. 11, 879 (2009)
K.P. Kaliappan, A.V. Subrahmanyam, Org. Lett. 9, 1121 (2007)
S.F. Martin, Pure Appl. Chem. 75, 63 (2003)
L. Nicolas, P. Angibaud, I. Stansfield, P. Bonnet, L. Meerpoel, S. Reymond, J. Cossy, Angew. Chem. Int. Ed. 51, 11101 (2012)
T.F. Jamison, S. Shambayati, W.E. Crowe, S.L. Schreiber, J. Am. Chem. Soc. 119, 4353 (1997)
P. Li, J. Yang, K. Zhao, J. Org. Chem. 64, 2259 (1999)
S.R. Angle, S.L. White, Tetrahedron Lett. 41, 8059 (2000)
T.R. Hoye, Z. Ye, J. Am. Chem. Soc. 1996, 118 (1801)
S. Baker, J. Canadian, Chem. 31, 821 (1953)
J.A. Marshall, J.J. Sabatini, Org. Lett. 22, 4819 (2005)
S.U. Son, Y.K. Chung, S.-G. Lee, J. Org. Chem. 65, 6142 (2000)
X. Lu, Top. Catal. 35, 73 (2005)
A. Lei, G. Liu, X. Lu, J. Org. Chem. 67, 974 (2002)
Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, S. Yamaguchi, J. Org. Chem. 62, 776 (1997)
Y. Kozawa, M. Mori, Tetrahedron Lett. 43, 1499 (2002)
H. Yokoyama, Y. Hirai, Heterocycles 75, 2133 (2008)
S.F. Kirsch, L.E. Overman, J. Org. Chem. 70, 2859 (2005)
N.-Y. Zhu, D. Yang, J. Am. Chem. Soc. 129, 11688 (2007)
L.F. Tietze, H. Ila, H.P. Bell, Chem. Rev. 104, 3453 (2004)
A.B. Dounay, L.E. Overman, Chem. Rev. 103, 2945 (2003)
C. Bolm, J.P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. Int. Ed. 40, 3284 (2001)
H. Alper, N. Hamel, Tetrahedron Lett. 28, 3237 (1987)
M.-D. Wang, S. Calet, H. Alper, J. Org. Chem. 54, 20 (1989)
T. Kondo, T.-A. Mitsudo, Chem. Rev. 100, 3205 (2000)
Y. Geng, A. Fechtenkötter, K. Mullen, J. Mater. Chem. 11, 1634 (2001)
K. Kobayashi, T. Shirasaka, A. Sato, E. Horn, N. Furukawa, Angew. Chem. Int. Ed. 38, 3483 (1999)
Vollhardt, K.P.C., Naiman, A. U.S. Pat. Appl. 886119 (1978); Chem. Abstr. 1979, 90, 186806d
Vollhardt, K.P.C., Naiman, A. U.S. Pat. Appl. 54926 (1982) [U.S.4 328343, 1982]; Ref. Zh. Khim. 1983, 11, H183П; Chem. Abstr. 1980, 93, 95139j
H. Lu, J. Tao, J.E. Jones, L. Wojtas, X.P. Zhang, Org. Lett. 12, 1248 (2010)
H. Lu, V. Subbarayan, J. Tao, X.P. Zhang, Organometallics 29, 389 (2010)
T.G. Driver, Org. Biomol. Chem. 8, 3831 (2010)
D.U. Miodragovic, G.A. Bogdanovic, Z.M. Miodragovic, M.D. Radulovic, S.B. Novakovic, G.N. Kaluđerovic, H. Kozłowski, J. Inorg. Biochem. 100, 1568 (2006)
J.M. Sprague, A.H. Land, C. Ziegler, J. Am. Chem. Soc. 68, 2155 (1946)
M. Baumann, I.R. Baxendale, S.V. Ley, N. Nikbin, Beilstein J. Org. Chem. 7, 442 (2011)
H. Bonnemann, R. Brinkman, H. Schenkluhn, Synthesis 8, 575 (1974)
K.P.C. Vollhardt, R.G. Bergman, J. Am. Chem. Soc. 96, 4996 (1974)
Kayushina, E.H., Levin, D.Z., Mortikov, E.S., Promonenkov, V. K. Ser. Khim. 1986, 1625
Kayushina, E.H., Mortikov, E.S., Promonenkov, V.K., Levin, D.Z. Moskva (VDNKh), 1985, S. 69
L. Jimenez-Gonzalez, S. Garcia-Munoz, M. Alvarez-Corral, M. Munoz-Dorado, I. Rodriguez-Garcia, Chem. Eur. J. 12, 8762 (2006)
Wakatsuki, Y., Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 8, 280
Y. Taarit, Y. Diab, B. Elleuch, M. Kerkani, M. Chihaoul, J. Chem. Soc., Chem. Commun. 5, 402 (1986)
H. Bonnemann, Angew. Chem. Int. Ed. 90, 517 (1978)
H. Bonnemann, R. Brinkmann, Synthesis 9, 600 (1975)
D. Tatone, T.C. Dich, R. Nacco, C. Botteghi, J. Org. Chem. 40, 2987 (1975)
U. Azzena, G. Chelluci, G. Delogu, C. Botteghi, Gazz. Chim. Ital. 116, 307 (1986)
H. Bonnemann, G. Natarajan, K.E. Erdolund, Petrochem. 33, 328 (1980)
R.E. Geiger, M. Lalonde, H. Stoller, K. Schleich, Helv. Chim. Acta 67, 1274 (1984)
B. Heller, J. Reihsig, W. Schulz, G. Oehme, Appl. Organomet. Chem. 7, 641 (1993)
H. Bonnemann, W. Brijoux, R. Brinkmann, W. Meurers, Helv. Chim. Acta 67, 1616 (1984)
M.D. Wang, H. Alper, J. Am. Chem. Soc. 114, 7018 (1992)
J.A. Varela, C. Saa, Chem. Rev. 103, 3787 (2003)
Y. Nakao, Synthesis 20, 3209 (2011)
A.W. Fatland, B.E. Eaton, Org. Lett. 2, 3131 (2000)
C.A. Parnell, K.P.C. Vollhardt, Tetrahedron 41, 5791 (1985)
Selimov, F.A., Khafizov, V.R., Dzhemilev, U. M. Ser. Khim. 1985, 1847
Selimov, F.A., Khafizov, V.R., Dzhemilev, U.M. Khim. Geterotsykl. Soedin. 1984, 360
A.E. Chichibabin, Orochko D.I. Zh, Russ. Khim. Obshch. 62, 1201 (1930)
Selimov, F.A., Akhmetov, A.Zh., Dzhemilev, U.M. Izv. AN SSSR, Ser. Khim. 1987, 2042
Dzhemilev, U.M., Selimov, F.A., Akhmetov, A.Zh. Soviet Union Pat.1 286594 (1987); From Otkrytiya, Izobret. 1987, (4), 95; Chem. Abstr. 1987, 106, 213772x
S. Kantevari, M.V. Chary, S.V.N. Vuppalapati, N. Lingaiah, J. Heterocycl. Chem. 45, 1099 (2008)
P. Hong, H. Yamazaki, Tetrahedron Lett. 15, 1333 (1977)
R.L. Hillard, K.P. Vollhardt, J. Am. Chem. Soc. 99, 4058 (1977)
Y. Wakatsuki, H. Yamazaki, Tetrahedron Lett. 14, 3383 (1973)
U. Groth, T. Huhn, C. Kesenheimer, A. Kalogerakis, Synlett 11, 1758 (2005)
I. Mohammadpoor-Baltork, S. Tangestaninejad, M. Moghadam, V. Mirkhani, S. Anvar, A. Mirjafari, Synlett 20, 3104 (2010)
L. Li, W.D. Jones, J. Am. Chem. Soc. 129, 10707 (2007)
S. Kotha, N. Sreenivasachary, Bioorg. Med. Chem. Lett. 10, 1413 (2000)
J. Efskind, K. Undheim, Tetrahedron Lett. 44, 2837 (2003)
S. Kotha, E. Brahmachary, K. Lahiri, Eur. J. Org. Chem. 22, 4741 (2005)
Y. Watanabe, N. Suzuki, Y. Tsuji, S.C. Shim, T. Mitsudo, Bull. Chem. Soc. Jpn 55, 1116 (1982)
Y. Watanabe, Y. Tsuji, J. Shida, Bull. Chem. Soc. Jpn 57, 435 (1984)
Y. Watanabe, K. Takatsuki, S.C. Shim, T. Mitsudo, Y. Takegami, Bull. Chem. Soc. Jpn 51, 3397 (1978)
J. Jacob, W.D. Jones, J. Org. Chem. 68, 3563 (2003)
Y. Watanabe, Y. Tsuji, Y. Ohsugi, J. Shida, Bull. Chem. Soc. Jpn 56, 2452 (1983)
A.R. Jagdale, R.S. Reddy, Sudalai A. Tetrahedron Asymmetry 20, 335 (2009)
A.R. Jagdale, R.S. Reddy, A. Sudalai, Org. Lett. 11, 803 (2009)
D.S. Bose, R.K. Kumar, Heterocycles 68, 549 (2006)
T. Joh, N. Hagihara, Tetrahedron Lett. 42, 4199 (1967)
R.F. Heck, D.S. Breslow, J. Am. Chem. Soc. 83, 1097 (1961)
H. Kumobayashi, S. Akutagawa, S. Otsuka, J. Am. Chem. Soc. 100, 3949 (1978)
H. Alper, D.H. Abbayes, D.D.J. Roches, Organometal. Chem. 121, 31 (1976)
H. Bonnemann, B. Bogdanovic, R. Brinkmann, Angew. Chem. Int. Ed. 95, 749 (1983)
Y. Wakatsuki, H. Yamazaki, Bull. Chem. Soc. Jpn 58, 2715 (1985)
G. Vitulli, S. Bertozzi, R. Lazzaroni, P.J. Salvadori, Organometal. Chem. 307, C35 (1986)
P. Chopade, J. Louie, Adv. Synth. Catal. 348, 2307 (2006)
N. Schore, Chem. Rev. 88, 1081 (1988)
J.A. Varela, C. Saa, Synlett 17, 2571 (2008)
J.D. Brien, A. Naiman, P.K.C. Vollhardt, J. Chem. Soc., Chem. Commun. 2, 133 (1982)
G.P. Chiusoli, L. Pallini, G. Terenghi, Trans. Met. Chem. 8, 250 (1983)
Chiusoli, G.P., Pallini, L., Terenghi, G. Eur. Pat. Appl. EP 92288, 1983; Chem. Abstr. 1984, 100, 121035 g
Y. Zhou, J.A. Porco, J.K. Snyder, Org. Lett. 9, 393 (2007)
J.A. Varela, L. Castedo, M. Maestro, J. Mahia, C. Saa, Chem. Eur. J. 7, 5203 (2001)
L.V.R. Bonaga, H.C. Zhang, A.F. Moretto, H. Ye, D.A. Gauthier, J. Li, G.C. Leo, B.E. Maryanoff, J. Am. Chem. Soc. 127, 3473 (2005)
J.A. Varela, L. Castedo, V. Saa, Org. Lett. 1, 2141 (1999)
J.A. Varela, L. Castedo, V. Saa, J. Org. Chem. 62, 4189 (1997)
A. Naiman, K.P.C. Vollhardt, Angew. Chem. Int. Ed. 89, 758 (1977)
G. Vitulli, S. Bertozzi, M. Vignali, R. Lazzaroni, P.J. Salvadori, Organometal. Chem. 326, C33 (1987)
Selimov, F.A., Khafizov, V.R., Dzhemilev, U.M. Izv. AN SSSR, Ser. Khim. 1983, 1885
K.P.C. Vollhardt, Angew. Chem. Int. Ed. 96, 525 (1984)
M.J. Eichberg, R.L. Dorta, D.B. Grotjahn, K. Lamottke, M. Schmidt, K.P.C. Vollhardt, J. Am. Chem. Soc. 123, 9324 (2001)
R. Boese, A.P.V. Sickle, K.P.C. Vollhardt, Synthesis 12, 1374 (1994)
R. Grigg, V. Sridharan, J. Wang, J. Xu, Tetrahedron 56, 8967 (2000)
A.F. Moretto, H.-C. Zhang, B.E. Maryanoff, J. Am. Chem. Soc. 123, 3157 (2001)
H. Alper, H. Arzoumanian, J.-F. Petrignani, M.S. Maldonado, J. Chem. Soc., Chem. Commun. 6, 340 (1985)
Y. Kamiya, K. Kawato, H. Ohta, Chem. Lett. 9, 1549 (1980)
L. Nagarapu, S. Kantevari, V.C. Mahankhali, S. Apuri, Catal. Commun. 8, 1173 (2007)
A. Das, A. Kulkarni, B. Torok, Green Chem. 14, 17 (2012)
K. Takai, M. Yamada, K. Utimoto, Chem. Lett. 24, 851 (1995)
J.V. Ruppel, R.M. Kamble, X.P. Zhang, Org. Lett. 9, 4889 (2007)
C.G. Espino, P.M. When, J. Chow, J. Du Bois, J. Am. Chem. Soc. 123, 6935 (2001)
B. Alcaide, P. Almendros, Eur. J. Org. Chem. 16, 3377 (2004)
B. Alcaide, P. Almendros, Chem. Rec. 11, 311 (2011)
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Kaur, N. Cobalt-catalyzed C–N, C–O, C–S bond formation: synthesis of heterocycles. J IRAN CHEM SOC 16, 2525–2553 (2019). https://doi.org/10.1007/s13738-019-01731-1
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DOI: https://doi.org/10.1007/s13738-019-01731-1