Abstract
This chapter reviews the synthesis of thioamide transition metal complexes and their structural features. The coordination chemistry of this group of ligands is unique due to their versatility of coordination states, such as monodentate, bridging, and chelating modes, including pincer ligands and scorpionate ligands. Further, some thioamide complexes can be used for applications in various areas such as chemical-sensor materials, tunable redox-potentials complexes, polymer hybrid luminescence materials, building blocks for multinuclear complexes, and catalysts for several coupling reactions.
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References
H.-J. Lee, Y.-S. Choi, K.-B. Lee, J. Park, C.-J. Yoon, J. Phys. Chem. A 106, 7010–7017 (2002)
G.F. Bordwell, Acc. Chem. Res. 21, 456–463 (1988)
F.G. Bordwell, G.-Z. Ji, J. Am. Chem. Soc. 113, 8398–8401 (1991)
Z. Mirjafary, L. Ahmadi, M. Moradi, H. Saeidian, RSC Adv. 5, 78038–78046 (2015)
A. Ranskiy, N. Didenko, O. Gordienko, Chem. Chem. Technol. 11, 11–18 (2017)
M.H. Habibi, S. Tangestaninejad, A. Fallah-shojaie, I. Mohammadpoor-baltork, S.F. Tayyari, G. Emtiazi, R. Hamidimotlagh, J. Coord. Chem. 58, 955–962 (2005)
D. Moran, K. Sukcharoenphon, R. Puchta, H.F. Schaefer III, P.V.R. Schleyer, C.D. Hoff, J. Org. Chem. 67, 9061–9069 (2002)
G. Dyson, A. Hamilton, B. Mitchell, G.R. Owen, Dalton Trans., 6120–6126 (2009)
P. Halder, S. Ghorai, S. Banerjee, B. Mondal, A. Rana, Dalton Trans. 46, 13739–13744 (2017)
T. Hamaguchi, K. Ujimoto, I. Ando, Inorg. Chem. 46, 10455–10457 (2007)
D. Milstein, J.C. Calabrese, I.D. Williams, J. Am. Chem. Soc. 108, 6387–6389 (1986)
J.C. Lee, E. Peris, R.H. Crabtree, A.L. Rheingold, R.H. Crabtree, J. Am. Chem. Soc. 116, 11014–11019 (1994)
S. Park, R. Ramachandran, A.J. Lough, R.H. Morris, J. Chem. Soc. Chem. Commun., 2201–2202 (1994)
S. Park, A.J. Lough, R.H. Morris, Inorg. Chem. 35, 3001–3006 (1996)
K.N. Kouroulis, S.K. Hadjikakou, N. Kourkoumelis, M. Kubicki, L. Male, M. Hursthouse, S. Skoulika, A.K. Metsios, V.Y. Tyurin, A.V. Dolganov, E.R. Milaeva, N. Hadjiliadis, Dalton Trans., 10446–10456 (2009)
K. Fukumoto, A. Sakai, T. Oya, H. Nakazawa, Chem. Commun. 48, 3809–3811 (2012)
K. Fukumoto, A. Sakai, K. Hayasaka, H. Nakazawa, Organometallics 32, 2889–2892 (2013)
M.N. Xanthopoulou, S.K. Hadjikakou, N. Hadjiliadis, E.R. Milaeva, J.A. Gracheva, V. Yu, N. Kourkoumelis, K.C. Christoforidis, A.K. Metsios, S. Karkabounas, K. Charalabopoulos, Eur. J. Med. Chem. 43, 327–335 (2008)
A.L. Catherall, S. Harris, M.S. Hill, A.L. Johnson, M.F. Mahon, Cryst. Growth Des. 17, 5544–5551 (2017)
A. Buffard, B. Nadal, H. Heuclin, G. Patriarche, B. Dubertret, New J. Chem. 39, 90–93 (2015)
H. Brunner, T. Zwack, M. Zabel, Z Krist. NCS 217, 551–553 (2002)
C. Alagöz, D.J. Brauer, F. Mohr, J. Organomet. Chem. 694, 1283–1288 (2009)
Y. Sekioka, S. Kaizaki, J.M. Mayer, T. Suzuki, Inorg. Chem. 44, 8173–8175 (2005)
V. Miranda-Soto, J.J. Pérez-Torrente, L.A. Oro, F.J. Lahoz, M. Luisa MartÃn, M. Parra-Hake, D.B. Grotjahn, Organometallics 25, 4374–4390 (2006)
K. Ogata, A. Toyota, J. Organomet. Chem. 692, 4139–4146 (2007)
T. Satoh, M. Miura, Chem. Lett. 36, 200–205 (2007)
H. Mizuno, M. Nonoyama, Polyhedron 9, 1287–1292 (1990)
M. Nonoyama, Transit. Met. Chem. 15, 366–370 (1990)
M. Nonoyama, K. Suzuki, Synth. React. Inorg. Met. Org. Chem. 23, 29–37 (1993)
M. Fukazawa, M. Kita, M. Nonoyama, Polyhedron 13, 1609–1617 (1994)
S. Takahashi, M. Nonoyama, Transit. Met. Chem. 20, 528–532 (1995)
M. Nonoyama, K. Nonoyama, Synth. React. Inorg. Met. Org. Chem. 25, 569–574 (1995)
Y. Nojima, M. Nonoyama, Polyhedron 15, 3795–3809 (1996)
W.B. Yu, P.F. Cui, W.X. Gao, G.X. Jin, Coord. Chem. Rev. 350, 300–319 (2017)
B. Xu, Y. Wang, Z. Yao, G. Jin, Dalton Trans. 44, 1530–1533 (2015)
P.-F. Cui, Y.-J. Lin, G.-X. Jin, Dalton Trans. 46, 15535–15540 (2017)
Y.P. Wang, L. Zhang, Y.-J. Lin, Z.-H. Li, G.-X. Jin, Chem. A Eur. J. 23, 1814–1819 (2017)
S.M. Meier, M. Hanif, Z. Adhireksan, V. Pichler, M. Novak, E. Jirkovsky, M.A. Jackupec, V.B. Arion, C.A. Davey, B.K. Keppler, C.G. Hartinger, Chem. Sci. 4, 1837–1846 (2013)
E. Sindhuja, R. Ramesh, N. Dharmaraj, Y. Liu, Inorg. Chim. Acta 416, 1–12 (2014)
K. Lyczko, M. Lyczko, S. Meczynska-Wielgosz, M. Kruszewski, J. Mieczkowski, J. Organomet. Chem. 866, 59–71 (2018)
P.-H. Leung, Y. Qin, G. He, K.F. Mok, J.J. Vittal, J. Chem. Soc., Dalt Trans., 309–314 (2001)
D. Pandiarajan, R. Ramesh, J. Organomet. Chem. 723, 26–35 (2013)
R.R. Kumar, R. Ramesh, J.G. Małecki, New J. Chem. 41, 9130–9141 (2017)
M. Albrecht, G. van Koten, Angew. Chem. Int. Ed. 40, 3750–3781 (2001)
G. van Koten, Top. Organomet. Chem. 40, 1–20 (2013)
E. Peris, R.H. Crabtree, Chem. Soc. Rev. 47, 1957–1968 (2018)
G. van Koten, J. Organomet. Chem. 730, 156–164 (2013)
O.S. Wenger, Chem. Rev. 113, 3686–3733 (2013)
L.A. van de Kuil, H. Luitjes, S.D.M. Grove, J.W. Zwikker, J.G.M. van der Linden, A.M. Roelofsen, L.W. Jenneskens, W. Drenth, G. van Koten, Organometallics 13, 468–477 (1994)
M. Contel, M. Stol, M.A. Casado, Klink G.P.M. Van, D.D. Ellis, A.L. Spek, G. van Koten, Organometallics 21, 4556–4559 (2002)
P. Steenwinkel, R.A. Gossage, T. Maunula, D.M. Grove, G. van Koten, Chem. Eur. J. 4, 763–768 (1998)
T. Kanbara, K. Okada, T. Yamamoto, H. Ogawa, T. Inoue, J. Organomet. Chem. 689, 1860–1864 (2004)
M. Akaiwa, T. Kanbara, H. Fukumoto, T. Yamamoto, J. Organomet. Chem. 690, 4192–4196 (2005)
K. Okamoto, T. Kanbara, T. Yamamoto, Chem. Lett. 35, 558–559 (2006)
J. Kuwabara, G. Munezawa, K. Okamoto, T. Kanbara, Dalton Trans. 39, 6255–6261 (2010)
T. Koizumi, T. Teratani, K. Okamoto, T. Yamamoto, Y. Shimoi, T. Kanbara, Inorg. Chim. Acta 363, 2474–2480 (2010)
T. Teratani, T. Koizumi, T. Yamamoto, K. Tanaka, T. Kanbara, Dalton Trans. 40, 8879–8886 (2011)
K. Okamoto, J. Kuwabara, T. Kanbara, J. Organomet. Chem. 696, 1305–1309 (2011)
Y. Komiyama, J. Kuwabara, T. Kanbara, Organometallics 33, 885–891 (2014)
H. Wang, J. Liu, Y. Deng, T. Min, G. Yu, X. Wu, Z. Yang, A. Lei, Chem. Eur. J. 15, 1499–1507 (2009)
V.A. Kozlov, D.V. Aleksanyan, Y.V. Nelyubina, K.A. Lyssenko, E.I. Gutsul, L.N. Puntus, A.A. Vasil’ev, P.V. Petrovskii, I.L. Odinets, Organometallics 27, 4062–4070 (2008)
D.V. Aleksanyan, V.A. Kozlov, Y.V. Nelyubina, K.A. Lyssenko, L.N. Puntus, E.I. Gutsul, N.E. Shepel, A.A. Vasil’ev, P.V. Petrovskii, I.L. Odinets, Dalton Trans. 40, 1535–1546 (2011)
D.V. Aleksanyan, Z.S. Klemenkova, A.A. Vasil’ev, A.Y. Gorenberg, Y.V. Nelyubina, V.A. Kozlov, Dalton Trans. 44, 3216–3226 (2015)
J. Kuwabara, T. Kanbara, J. Photopolym. Sci. Tech. 21, 349–353 (2008)
K. Okamoto, T. Yamamoto, M. Akita, A. Wada, T. Kanbara, Organometallics, 3307–3310 (2009)
Y. Ogawa, A. Taketoshi, J. Kuwabara, K. Okamoto, T. Fukuda, T. Kanbara, Chem. Lett. 39, 385–387 (2010)
K. Okamoto, T. Yamamoto, T. Kanbara, J. Nanosci. Nanotechnol. 9, 646–649 (2009)
J. Kuwabara, Y. Ogawa, A. Taketoshi, T. Kanbara, J. Organomet. Chem. 696, 1289–1293 (2011)
Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Soc. Rev. 40, 5361–5388 (2011)
H. Honda, Y. Ogawa, J. Kuwabara, T. Kanbara, Eur. J. Inorg. Chem. 1865–1869 (2014)
H. Honda, J. Kuwabara, T. Kanbara, J. Organomet. Chem. 772–773, 139–142 (2014)
O.R. Luca, S.J. Konezny, J.D. Blakemore, D.M. Colosi, S. Saha, G.W. Brudvig, V.S. Batista, R.H. Crabtree, New J. Chem. 36, 1149–1152 (2012)
P. Kang, T.J. Meyer, M. Brookhart, Chem. Sci. 4, 3497–3502 (2013)
K. Umehara, S. Kuwata, T. Ikariya, J. Am. Chem. Soc. 135, 6754–6757 (2013)
H. Tanaka, K. Arashiba, S. Kuriyama, A. Sasada, K. Nakajima, K. Yoshizawa, Y. Nishibayashi, Nat. Commun. 5, 3737 (2014)
E.A. Bielinski, P.O. Lagaditis, Y. Zhang, B.Q. Mercado, C. Würtele, W.H. Bernskoetter, N. Hazari, S. Schneider, J. Am. Chem. Soc. 136, 10234–10237 (2014)
T. Teratani, T. Koizumi, T. Yamamoto, T. Kanbara, Inorg. Chem. Commun. 14, 836–838 (2011)
C.-H. Wang, N.N. Ma, X.-X. Sun, S.-L. Sun, Y.-Q. Qiu, P.-J. Liu, J. Phys. Chem. A 116, 10496–10506 (2012)
T. Suzuki, Y. Kajita, H. Masuda, Dalton Trans. 43, 9732–9739 (2014)
T. Suzuki, J. Matsumoto, Y. Kajita, T. Inomata, T. Ozawa, H. Masuda, Dalton Trans. 44, 1017–1022 (2015)
G. Dyson, A. Zech, B.W. Rawe, M.F. Haddow, A. Hamilton, G.R. Owen, Organometallics 30, 5844–5850 (2011)
A. Zech, M.F. Haddow, H. Othman, G.R. Owen, Organometallics 31, 6753–6760 (2012)
A. Iannetelli, G. Tizzard, S.J. Coles, G.R. Owen, Organometallics 37, 2177–2187 (2018)
K. Saha, R. Ramalakshmi, S. Gomosta, K. Pathak, V. Dorcet, T. Roisnel, J.-F. Halet, S. Ghosh, Chem. A Eur. J. 23, 9812–9820 (2017)
H. Baba, M. Nakano, Inorg. Chem. Commun. 17, 177–179 (2012)
K. Umakoshi, I. Kinoshita, A. Ichimura, S. Ooi, Inorg. Chem. 26, 3551–3556 (1987)
K. Umakoshi, I. Kinoshita, S. Ooi, Inorg. Chem. 29, 4005–4010 (1990)
M. Kato, A. Omura, A. Toshikawa, S. Kishi, Y. Sugimoto, Angew. Chem. Int. Ed. 41, 3183–3185 (2002)
T. Koshiyama, A. Omura, M. Kato, Chem. Lett. 33, 1386–1387 (2004)
Z. Wang, L. Jiang, Z.-P. Liu, C.R.R. Gan, Z. Liu, X.-H. Zhang, J. Zhao, T.S.A. Hor, Dalton Trans. 41, 12568–12576 (2012)
V. Sicilia, J. Fornie, J.M. Casas, A. Mart, J.A. Lo, C. Larraz, P. Borja, C. Ovejero, D. Tordera, H. Bolink, Inorg. Chem. 3427–3435 (2012)
V. Sicilia, P. Borja, A. MartÃn, Inorganics 61188, 508–523 (2014)
M.D. Aseman, S.M. Nabavizadeh, H.R. Shahsavari, M. Rashidi, RSC Adv. 5, 22692–22702 (2015)
N. Maryam, H.R. Shahsavari, M.G. Haghighi, M.R. Halvagar, H. Samaneh, B. Notash, RSC Adv 6, 76463–76472 (2016)
Y. Shu, H. Lei, Y.N. Tan, M. Meng, X.C. Zhang, C.Y. Liu, Dalton Trans. 43, 14756–14765 (2014)
C. Jiang, P.J. Young, S. Brown-xu, J.C. Gallucci, M.H. Chisholm, Inorg. Chem. 56, 1433–1445 (2017)
T. Chivers, A. Downard, M. Parvez, G. Schatte, Organometallics 20, 727–733 (2001)
R. Kapoor, A. Kataria, P. Venugopalan, P. Kapoor, M. Corbella, M. RodrÃguez, I. Romero, A. Llobet, Inorg. Chem. 43, 6699–6709 (2004)
J. Liu, H. Wang, H. Zhang, X. Wu, H. Zhang, Y. Deng, Z. Yang, A. Lei, Chem. Eur. J. 15, 4437–4445 (2009)
L.E. Karagiannidis, P.A. Gale, M.E. Light, M. Massi, M.I. Ogden, Dalton Trans. 40, 12097–12105 (2011)
J. Du, Y. Wei, X. Yang, H. Zhu, Inorg. Chem. Commun. 93, 37–41 (2018)
Z. Xiong, N. Wang, M. Dai, A. Li, J. Chen, Z. Yang, Org. Lett. 6, 3337–3340 (2004)
E. Sindhuja, R. Ramesh, S. Balaji, Y. Liu, Organometallics 33, 4269–4278 (2014)
M.U. Raja, R. Ramesh, Y. Liu, Tetrahedron Lett. 52, 5427–5430 (2011)
E. Sindhuja, R. Ramesh, Y. Liu, Dalton Trans. 41, 5351–5361 (2012)
M.U. Raja, R. Ramesh, J. Organomet. Chem. 699, 5–11 (2012)
A. Kanchanadevi, R. Ramesh, D. Semeril, J. Organomet. Chem. 808, 68–77 (2016)
T. Satoh, M. Masahiro, J. Synth. Org. Chem. Jpn. 64, 1199–1207 (2006)
G. Shi, Y. Zhang, Adv. Synth. Catal. 356, 1419–1442 (2014)
R. Das, S. Kumar, M. Kapur, Eur. J. Org. Chem., 5439–5459 (2017)
Y. Mutoh, M. Sakigawara, I. Niiyama, S. Saito, Y. Ishii, Organometallics 33, 5414–5422 (2014)
K. Inamoto, C. Hasegawa, K. Hiroya, T. Doi, Org. Lett. 10, 5147–5150 (2008)
B. Saraiah, V. Gautam, A. Acharya, M.A. Pasha, I. Hiriyakkanavar, Eur. J. Org. Chem., 5679–5688 (2017)
Y. Yokoyama, Y. Unoh, R.A. Bohmann, T. Satoh, K. Hirano, C. Bolm, M. Miura, Chem. Lett. 44, 1104–1106 (2015)
T. Yamauchi, F. Shibahara, T. Murai, Org. Lett. 17, 5392–5395 (2015)
F. Shibahara, Y. Asai, T. Murai, Asian J. Org. Chem. 7, 1323–1326 (2018)
K.-X. Tang, C.-M. Wang, T.-H. Gao, C. Pan, L.-P. Sun, Org. Chem. Front. 11, 2167–2169 (2017)
J.E. Spangler, Y. Kobayashi, P. Verma, D. Wang, J. Yu, J. Am. Chem. Soc. 137, 11876–11879 (2015)
P. Jain, P. Verma, G. Xia, J. Yu, Nat. Chem. 9, 140–144 (2016)
H. Bonds, G. Song, Z. Zheng, Y. Wang, X. Yu, Org. Lett. 18, 6002–6005 (2016)
P.W. Tan, A.M. Mak, M.B. Sullivan, D.J. Dixon, J. Seayad, Angew. Chem. Int. Ed. 56, 16550–16554 (2017)
L. Zhong’e, Z. Runsheng, S. Daqing, Chem. Res. Chin. Univ. 7, 184–187 (1991)
O. Ortet, A.P. Paiva, Hydrometallurgy 151, 33–41 (2015)
M. Yamada, M.R. Gandhi, D. Sato, Y. Kaneta, N. Kimura, Ind. Eng. Chem. 55, 8914–8921 (2016)
T. Kanbara, Y. Kawai, K. Hasegawa, H. Morita, T. Yamamoto, J. Polym. Sci. Part A Polym. Chem. 39, 3739–3750 (2001)
S. Kagaya, E. Sato, I. Masore, K. Hasegawa, T. Kanbara, Chem. Lett. 32, 622–623 (2003)
S. Kagaya, E. Tanaka, N. Kawai, I. Masore, E. Sato, K. Hasegawa, M. Kishi, T. Kanbara, J. Inorg. Organomet. Polym. 19, 67–73 (2009)
N.N. Chopabaeva, E.E. Ergozhin, Russ. J. Appl. Chem. 81, 231–235 (2008)
F.Z. Ramdane, G. Tabak, K. Nassima, A. Benaboura, Polym. Sci. Ser. B 59, 443–451 (2017)
S. Kagaya, H. Miyazaki, M. Ito, K. Tohda, T. Kanbara, J. Hazard. Mater. 175, 1113–1115 (2010)
C.M.V. Stålhandske, C.I. Stålhandske, M. Sandström, I. Persson, Inorg. Chem. 36, 3167–3173 (1997)
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Okamoto, K., Kuwabara, J., Kanbara, T. (2019). Thioamide-Based Transition Metal Complexes. In: Murai, T. (eds) Chemistry of Thioamides. Springer, Singapore. https://doi.org/10.1007/978-981-13-7828-7_7
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