Recent Progress in the Main Group Complexes with the 2,6-Pyridinediimine

doi:10.6023/cjoc202211037

Abstract

2,6-Pyridinediimine (PDI) as a tridentate ligand with redox activity can coordinate to transition metals (TM), main group (MG) elements, lanthanides and actinides. Since the application of PDI-TM in olefin polymerization, there has been a great interest in the synthesis and application of PDI supported complexes. Due to the properties such as low cost, readily availability and low toxicity of the main group elements, the field of PDI-MG has been evolving rapidly recently. In this paper, the PDI-MG complexes are summarized according to the group number of the MG. At the same time, the synthetic methodology together with the reactivity of these reported PDI-MG complexes is summarized and the oxidation states of their ligands are emphatically analyzed. At present, compared with the development of PDI-TM, the research of low-valence PDI-MG is still in its infancy. Therefore, a comprehensive survey of these compounds could not only facilitate a comprehensive and systematic understanding of existing compounds, but also promote the development of new structures and reactivities.

Key words: 2,6-pyridinediimine, main group elements

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Xingxing Yang, Yonghao Fan, Jingjing Cui. Recent Progress in the Main Group Complexes with the 2,6-Pyridinediimine[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2338-2350.

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Fig. & Tab. 28

Scheme 1. Conformations of (a) free PDI ligands and (b) PDI-MG complexes

Scheme 2. (a) Tautomerizations of PDI ligands, and (b) an example of enamine tautomerization in a PDI ligand

Scheme 3. Selected examples demonstrating the synthesis of (a) symmetric and (b) asymmetric PDI ligands

Scheme 4. Five oxidation states of PDI ligands

Scheme 5. Definition of Δ values for PDI ligands

(PDI)ⁿ/n	Δ_calcd/nm	Δ_exp/nm
0	0.0184	0.0185±0.002
1^－	0.0120	0.0120±0.002
2^－	0.0074	0.0065
3^－	0.0001	—
4^－	－0.0039	—

Table 2. Δ values of PDI-Zn(II) complexes

Scheme 6. Synthesis of compounds 9 and 10

Scheme 7. Synthesis of compound 11a

Scheme 8. Synthesis of compounds 11b, 11c and 11d

Scheme 9. Synthesis of compounds 15~17

Scheme 10. Synthesis of compounds 18a/18b, 19a/19b, 20, 21a/21b

Scheme 11. Synthesis of compounds 22 and 23

Scheme 12. Synthesis of compounds 24~26

Scheme 13. Synthesis of compound 27

Scheme 14. Synthesis of compounds 28 and 29

Scheme 15. Synthesis of compound 30

Scheme 16. Synthesis of compound 31

Scheme 17. Synthesis of compound 32

Scheme 18. Synthesis of compounds 33~35

Scheme 19. Oxidation state structures of compounds 32~35

Scheme 20. Synthesis of compounds 37, 38, 40 and 41

Scheme 21. Synthesis of compounds 42~44

Scheme 22. Synthesis of compounds 45~47

Scheme 23. Oxidation state structures of compounds 45~47

Scheme 24. Oxidation/reduction reactions of PDI-MG complexes

Scheme 25. Mechanism of selective removal of H2 and CO2 by reaction of compound 18b with formic acid

Scheme 26. Insertion and elimination of CO2 from 18b

Scheme 27. The reaction of compound 19b to activate the N—H bond

References 86

[1]	Small, B. L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 4049. doi: 10.1021/ja9802100
[2]	Flisak, Z.; Sun, W. H. ACS Catal. 2015, 5, 4713. doi: 10.1021/acscatal.5b00820
[3]	Sieh, D.; Schlimm, M.; Andernach, L.; Angersbach, F. Eur. J. Inorg. Chem. 2012, 444.
[4]	Bianchini, C.; Giambastiani, G.; Rios, I. G.; Mantovani, G.; Meli, A.; Segarra, A. M. Coord. Chem. Rev. 2006, 250, 1391. doi: 10.1016/j.ccr.2005.12.018
[5]	Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13340. doi: 10.1021/ja064711u pmid: 17031930
[6]	Kennedy, C. R.; Chirik, P. J. Adv. Synth. Catal. 2020, 362, 404. doi: 10.1002/adsc.201901289 pmid: 32431586
[7]	Jiao, M.; Wang, Z.; Zhang, B.; Chen, B. Z. New J. Chem. 2022, 46, 4052. doi: 10.1039/D1NJ05646H
[8]	Shejwalkar, P.; Rath, N. P.; Bauer, E. B. Synthesis 2014, 46, 57. doi: 10.1055/s-00000084
[9]	Liu, P.; Yan, M.; He, R. Appl. Organomet. Chem. 2010, 24, 131.
[10]	Chiericato, Jr. G.; Arana, C. R.; Casado, C.; Cuadrado, I.; Abruna, H. D. Inorg. Chim. Acta 2000, 32-42, 300.
[11]	Jiang, J.; Kucernak, A. Electrochim. Acta 2002, 47, 1967. doi: 10.1016/S0013-4686(02)00042-7
[12]	Fan, R. Q.; Chen, H.; Wang, P.; Yang, Y. L.; Yin, Y. B.; Hasi, W. J. Coord. Chem. 2010, 63, 1514. doi: 10.1080/00958972.2010.481715
[13]	Fan, R.; Yang, Y.; Yin, Y. Inorg. Chem. 2009, 48, 6034. doi: 10.1021/ic900339u
[14]	Shaver, M. P.; Hanhan, M. E. Chem. Commun. 2010, 46, 2127. doi: 10.1039/b922202b
[15]	Hu, X.; Li, J. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4378. doi: 10.1002/pola.26853
[16]	Perry, M. R.; Allan, L. E. Dalton Trans. 2013, 42, 9157. doi: 10.1039/c3dt32625j
[17]	Anderson, N. H.; Odoh, S. O.; Yao, Y. Nat. Chem. 2014, 6, 919. doi: 10.1038/nchem.2009
[18]	Kaim, W. Eur. J. Inorg. Chem. 2012, 343.
[19]	Bruin, B.; Bill, E.; Bothe, E. Inorg. Chem. 2000, 39, 2936. pmid: 11232835
[20]	Tidwell, J. R.; Dutton, J. L.; Martin, C. D. Dalton Trans. 2021, 50, 11716. doi: 10.1039/d1dt02085d pmid: 34612308
[21]	Bass, T. M.; Carr, C. R.; Berben, L. A. Inorg. Chem. 2020, 59, 13517. doi: 10.1021/acs.inorgchem.0c01908
[22]	Tidwell, J. R.; Martin, C. D. Organometallics 2022, 41, 1197. doi: 10.1021/acs.organomet.2c00093
[23]	Myers, T. W.; Berben, L. A. J. Am. Chem. Soc. 2013, 135, 9988. doi: 10.1021/ja4032874
[24]	Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745. doi: 10.1021/cr068437y
[25]	Pelascini, F.; Wesolek, M.; Peruch, F.; Lutz, P. J. Eur. J. Inorg. Chem. 2006, 4309.
[26]	Wallenhorst, C.; Kehr, G.; Luftmann, H. Organometallics 2008, 27, 6547. doi: 10.1021/om800726y
[27]	Guo, L. H.; Gao, H. Y.; Zhang, L.; Zhu, F. M.; Wu, Q. Organometallics 2010, 29, 2118. doi: 10.1021/om9010356
[28]	Kleigrewe, N.; Steffen, W.; Blömker, T.; Kehr, G.; Fröhlich, R.; Wibbeling, B.; Bazan, G. C. J. Am. Chem. Soc. 2005, 127, 13955. pmid: 16201818
[29]	Steves, J. E.; Kennedy, M. D.; Chiang, K. P. Dalton Trans. 2009, 29, 1214.
[30]	Sun, W. H.; Zhao, W.; Yu, J.; Zhang, W.; Hao, X.; Redshaw, C. Macromol. Chem. Phys. 2012, 213, 1266. doi: 10.1002/macp.201200051
[31]	Magdzinski, E.; Gobbo, P.; Martin, C. D.; Workentin, M. S.; Ragogna, P. J. Inorg. Chem. 2012, 51, 8425. doi: 10.1021/ic300974u pmid: 22775510
[32]	Orrell, K. G.; Osborne, A. G.; Šik, V. Organomet. Chem. 1997, 530, 235. doi: 10.1016/S0022-328X(96)06661-2
[33]	Reeske, G.; Cowley, A. H. Chem. Commun. 2006, 46, 4856.
[34]	Martin, C. D.; Ragogna, P. J. Inorg. Chem. 2012, 51, 2947. doi: 10.1021/ic202213x pmid: 22339169
[35]	Martin, C. D.; Ragogna, P. J. Dalton Trans. 2011, 40, 11976. doi: 10.1039/c1dt11111f pmid: 21983569
[36]	Reardon, D.; Conan, F.; Gambarotta, S.; Yap, G.; Wang, Q. J. Am. Chem. Soc. 1999, 121, 9318. doi: 10.1021/ja990263x
[37]	Ionkin, A. S.; Marshall, W. J.; Adelman, D. J.; Fones, B. B.; Fish, B. M.; Schiffhauer, M. F.; Soper, P. D.; Waterland, R. L.; Spence, R. E.; Xie, T. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 585. doi: 10.1002/(ISSN)1099-0518
[38]	Small, B. L.; Brookhart, M.; Bennett, A. M. J. Am. Chem. Soc. 1998, 120, 4049. doi: 10.1021/ja9802100
[39]	Britovsek, G. J. P.; Gibson, V. C.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J.; Maddox, P. J. Chem. Commun. 1998, 7, 849.
[40]	Ma, Z.; Sun, W. H.; Li, Z. L.; Shao, C. X.; Hu, Y. L.; Li, X. H. Polym. Int. 2002, 51, 994. doi: 10.1002/(ISSN)1097-0126
[41]	Bart, S. C.; Chłopek, K.; Bill, E.; Bouwkamp, M. W.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13901. doi: 10.1021/ja064557b
[42]	Knijnenburg, Q.; Gambarotta, S.; Budzelaar, P. H. Dalton Trans. 2006, 46, 5442.
[43]	Römelt, C.; Weyhermüller, T.; Wieghardt, K. Coord. Chem. Rev. 2019, 380, 287. doi: 10.1016/j.ccr.2018.09.018
[44]	Brown, S. N. Inorg. Chem. 2012, 51, 1251. doi: 10.1021/ic202764j pmid: 22260321
[45]	Enright, D.; Gambarotta, S.; Yap, G. P.; Budzelaar, P. H. Angew. Chem., Int. Ed. 2002, 41, 3873. doi: 10.1002/1521-3773(20021018)41:20【-逻辑与-】lt;3873::AID-ANIE3873【-逻辑与-】gt;3.0.CO;2-8
[46]	Myers, T. W.; Sherbow, T. J.; Fettinger, J. C.; Berben, L. A. Dalton Trans. 2016, 45, 5989. doi: 10.1039/C5DT01541C
[47]	Addison, A. W.; Rao, T. N.; Reedijk, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349.
[48]	Arrowsmith, M.; Hill, M. S.; Kociok-Köhn, G. Organometallics 2010, 29, 4203. doi: 10.1021/om100649z
[49]	Dawkins, M. J. C.; Simonov, A. N.; Jones, C. Dalton Trans. 2020, 49, 6627. doi: 10.1039/D0DT01278E
[50]	Dawson, K.; Mallov, I.; Burchell, T.; Yap, G. P.; Richeson, D. S. Dalton Trans. 2010, 39, 1266. doi: 10.1039/B920047A
[51]	Jurca, T.; Lummiss, J.; Burchell, T. J.; Gorelsky, S. I.; Richeson, D. S. J. Am. Chem. Soc. 2009, 131, 4608. doi: 10.1021/ja901128q
[52]	Thompson, E. J.; Myers, T. W.; Berben, L. A. Angew. Chem., Int. Ed. Engl. 2014, 53, 14132. doi: 10.1002/anie.v53.51
[53]	Andrews, C. G.; Macdonald, C. L. B. Angew. Chem., Int. Ed. 2005, 44, 7453. doi: 10.1002/(ISSN)1521-3773
[54]	Cooper, B. F. T.; Macdonald, C. L. B. J. Organomet. Chem. 2008, 693, 1707. doi: 10.1016/j.jorganchem.2007.10.040
[55]	Hill, M. S.; Hitchcock, P. B. Chem. Commun. 2004, 16, 1818.
[56]	Jones, C.; Junk, P. C.; Platts, J. A.; Rathmann, D.; Stasch, A. Dalton Trans. 2005, 2497.
[57]	Baba, T.; Takeuchi, M.; Nakai, H. Chem. Phys. Lett. 2006, 424, 193. doi: 10.1016/j.cplett.2006.03.098
[58]	Jurca, T.; Korobkov, I.; Gorelsky, S. I.; Richeson, D. S. Inorg. Chem. 2013, 52, 5749. doi: 10.1021/ic302552v
[59]	Cordero, B.; Gomez, V.; Reves, M.; Echeverria, J.; Cremades, E.; Barragan, F.; Alvarez, S. Dalton Trans. 2008, 21, 2832.
[60]	Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024. doi: 10.1063/1.472902
[61]	Mayer, I. Int. J. Quantum Chem. 1986, 29, 73. doi: 10.1002/(ISSN)1097-461X
[62]	Reger, D. L.; Wright, T. D.; Smith, M. D.; Rheingold, A. L.; Kassel, S.; Concolino, T.; Rhagitan, B. Polyhedron 2002, 21, 1795. doi: 10.1016/S0277-5387(02)01058-6
[63]	Bailey, N. A.; Fenton, D. E.; Jackson, I. T.; Moody, R.; Barbarin, L. R. J. Chem. Soc., Chem. Commun. 1983, 23, 1462.
[64]	Harrowfield, J. M.; Miyamae, H.; Shand, T. M.; Skelton, B. W.; Soudi, A. A.; White, A. H. Aust. J. Chem. 1996, 49, 1051. doi: 10.1071/CH9961051
[65]	Soleilhavoup, M.; Bertrand, G. Chem 2020, 6, 1275. doi: 10.1016/j.chempr.2020.04.015
[66]	Schäfer, A.; Saak, W.; Haase, D.; Müller, T. Chem.-Eur. J. 2009, 15, 3945. doi: 10.1002/chem.v15:16
[67]	Singh, A. P.; Roesky, H. W.; Carl, E.; Stalke, D.; Demers, J. P.; Lange, A. J. Am. Chem. Soc. 2012, 134, 4998. doi: 10.1021/ja300563g
[68]	Flock, J.; Suljanovic, A.; Torvisco, A.; Schoefberger, W.; Gerke, B.; Pöttgen, R.; Fischer, R. C.; Flock, M. Chem.-Eur. J. 2013, 19, 15504. doi: 10.1002/chem.v19.46
[69]	Bart, S. C.; Chłopek, K.; Bill, E.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13901. doi: 10.1021/ja064557b
[70]	Khan, S.; Michel, R.; Dieterich, J. M.; Mata, R. A.; Roesky, H. W.; Demers, J. P.; Lange, A.; Stalke, D. J. Am. Chem. Soc. 2011, 133, 17889. doi: 10.1021/ja207538g
[71]	Zabula, A. V.; Pape, T.; Hepp, A. J. Am. Chem. Soc. 2008, 130, 5648. doi: 10.1021/ja801000b
[72]	Power, P. P. Nature 2010, 463, 171. doi: 10.1038/nature08634
[73]	Chu, T.; Belding, L.; Dudding, T.; Korobkov, I.; Nikonov, G. I. Angew. Chem., Int. Ed. 2014, 53, 2711. doi: 10.1002/anie.201309421
[74]	Lippens, P. E. Phys. Rev. B 1999, 60, 4576. doi: 10.1103/PhysRevB.60.4576
[75]	Greb, L. Eur. J. Inorg. Chem. 2022, e202100871.
[76]	Reeske, G.; Cowley, A. H. Chem. Commun. (Camb.) 2006, 16, 1784.
[77]	Yap, G. P. A.; Gambarotta, S. private communication to CCDC (no. 116252), 1999.
[78]	Chitnis, S. S.; LaFortune, J. H.; Cummings, H.; Liu, L. L.; Andrews, R.; Stephan, D. W. Organometallics 2018, 37, 4540. doi: 10.1021/acs.organomet.8b00686
[79]	Gray, P. A.; Braun, J. D.; Rahimi, N.; Herbert, D. E. Eur. J. Inorg. Chem. 2020, 2105.
[80]	Martin, C. D.; Jennings, M. C.; Ferguson, M. J.; Ragogna, P. J. Angew. Chem., Int. Ed. 2009, 48, 2210. doi: 10.1002/anie.200805198 pmid: 19137516
[81]	Pyykkö, P.; Atsumi, M. Chem.-Eur. J. 2009, 15, 186. doi: 10.1002/chem.200800987 pmid: 19058281
[82]	Mantina, M.; Chamberlin, A. C.; Valero, R.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2009, 113, 5806. doi: 10.1021/jp8111556
[83]	Martin, C. D.; Le, C. M.; Ragogna, P. J. J. Am. Chem. Soc. 2009, 131, 15126. doi: 10.1021/ja9073968 pmid: 19803516
[84]	Bonyhady, S. J.; Jones, C.; Nembenna, S.; Stasch, A.; Edwards, A. J.; McIntyre, G. J. Chem.-Eur. J. 2010, 16, 938. doi: 10.1002/chem.200902425 pmid: 19950340
[85]	Hicks, J.; Juckel, M.; Paparo, A.; Dange, D.; Jones, C. Organometallics 2018, 37, 4810. doi: 10.1021/acs.organomet.8b00803
[86]	Myers, T. W.; Berben, L. A. Chem. Sci. 2014, 5, 2771. doi: 10.1039/C4SC01035C

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