Cobalt catalyzed defunctionalization reactions: Review article

LJiljana Koračak; Vladimir Ajdačić

doi:10.2298/JSC240315045K

PDF (5.44 MB)

Published: Jul 5, 2024

Updated: 05.07.2024

DOI: https://doi.org/10.2298/JSC240315045K

Keywords:

decarbonylation decarboxylation dehalogenation desulfurization deoxygenation

LJiljana Koračak

Innovative Centre, Faculty of Chemistry, Ltd. Studentski Trg 12-16, 11158 Belgrade, Serbia

https://orcid.org/0000-0003-4892-1290

Vladimir Ajdačić

Vladimir Ajdačić Faculty of Chemistry, University of Belgrade, 11000 Belgrade, Serbia E-mail: ajdacic@chem.bg.ac.rs

https://orcid.org/0000-0002-3423-0862

Abstract

Catalytic defunctionalization of complex molecules has attracted significant attention in organic synthesis. This reaction enables common functional groups to serve as “traceless handles” for the new bond construction. In this mini-review, we have summarized the latest advances, methodologies and mechanistic insights into the selective cleavage of C–C and C–X bonds catalysed by cobalt complexes, shedding light on their increasing importance in modern chemical synthesis. The content of this review is categorized according to the type of functional group being removed from molecules.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

How to Cite

[1]

L. Koračak and V. Ajdačić, “Cobalt catalyzed defunctionalization reactions: Review article”, J. Serb. Chem. Soc., vol. 89, no. 6, pp. 785–806, Jul. 2024.

Issue

Vol. 89 No. 6 (2024)

Section

Organic Chemistry

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Funding data

Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja
Grant numbers 451-03-66/2024-03/200288

References

A. Modak, D. Maiti, Org. Biomol. Chem. 14 (2016) 21 (https://doi.org/10.1039/C5OB01949D)

Ž. Selaković, A. M. Nikolić, V. Ajdačić, I. M. Opsenica, Eur. J. Org. Chem. (2022) e202101265 (https://doi.org/10.1002/ejoc.202101265)

J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 110 (2010) 3552 (https://doi.org/10.1021/cr900354u)

J. S. Dickstein, J. M. Curto, O. Gutierrez, C. A. Mulrooney, M. C. Kozlowski, J. Org. Chem. 78 (2013) 4744 (https://doi.org/10.1021/jo400222c)

O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem. 69 (2004) 3173 (https://doi.org/10.1021/jo035834p)

J. F. Hooper, R. D. Young, A. S. Weller, M. C. Willis, Chem. Eur. J. 19 (2013) 3125 (https://doi.org/10.1002/chem.201204056)

M. Tobisu, R. Nakamura, Y. Kita, N. Chatani, J. Am. Chem. Soc. 131 (2009) 3174 (https://doi.org/10.1021/ja810142v)

N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 123 (2001) 4849 (https://doi.org/10.1021/ja0103501)

G. Domazetis, B. Tarpey, D. Dolphin, B. R. James, J. Chem. Soc., Chem. Commun. (1980) 939 (https://doi.org/10.1039/C39800000939)

B. Kokić, B. Vulović, M. Jović, A. Andrijević, V. Ajdačić, I. M. Opsenica, Eur. J. Org. Chem. 26 (2023) e202300997 (https://doi.org/10.1002/ejoc.202300997)

B. Kokić, Ž. Selaković, A. M. Nikolić, A. Andrijević, B. Anđelković, V. Ajdačić, I. M. Opsenica, Eur.J. Org.Chem. (2022) e202201112 (https://doi.org/10.1002/ejoc.202201112)

G. R. Lappin, J. D. Sauer, Alpha Olefns Applications Handbook, Marcel Dekker, New York, 1989 (ISBN:9780824778958)

I. T. Horváth, Chem. Rev. 118 (2018) 369 (https://doi.org/10.1021/acs.chemrev.7b00721)

R. A. Sheldon, J. K. Kochi, Org. React. 19 (2011) 279 (https://doi.org/10.1002/0471264180.or019.04)

T.Takeda, Modern Carbonyl Olefination: Methods and Applications; John Wiley & Sons, Hoboken, NJ, 2006 (ISBN:978-3-527-60538-5)

L. J. Gooßen, N. A. Rodríguez, Chem. Commun. (2004) 724 (https://doi.org/10.1039/B316613A)

A. John, M. O. Miranda, K. Ding, B. Dereli, M. A. Ortuño, A. M. LaPointe, G. W. Coates, C. J. Cramer, W. B. Tolman, Organometallics 35 (2016) 2391 (https://doi.org/10.1021/acs.organomet.6b00415)

A. John, M. A. Hillmyer, W. B. Tolman, Organometallics 36 (2017) 506 (https://doi.org/10.1021/acs.organomet.6b00940)

S. Maetani, T. Fukuyama, N. Suzuki, D. Ishihara, I. Ryu, Organometallics 30 (2011) 1389 (https://doi.org/10.1021/om1009268)

K. C. Cartwright, J. A. Tunge, ACS Catal. 8 (2018) 11801 (https://doi.org/10.1021/acscatal.8b03282)

K. C. Cartwright, E. Joseph, C. G. Comadoll, J. A. Tunge, Chem. Eur. J. 26 (2020) 12454 (https://doi.org/10.1002/chem.202001952)

X. Sun , J. Chen , T. Ritter , Nature Chem. 10 (2018) 1229 (https://doi.org/10.1038/s41557-018-0142-4)

V. T. Nguyen, V. D. Nguyen, G. C. Haug, H. T. Dang, S. Jin, Z. Li, C. Flores-Hansen, B. S. Benavides, H. D. Arman, O. V. Larionov, ACS Catal. 9 (2019) 9485 (https://doi.org/10.1021/acscatal.9b02951)

E. N. G. Marsh, M. W. Waugh, ACS Catal. 3 (2013) 2515 (https://doi.org/10.1021/cs400637t)

N. Terzić Jovanović, V. Ajdačić, J. Serb. Chem. Soc. 87 (2022) 669 (https://doi.org/10.2298/JSC220128024T)

H. Lu, T. Y. Yu, P. F. Xu, H. Wei, Chem. Rev. 121 (2021) 365 (https://doi.org/10.1021/acs.chemrev.0c00153)

S. Yuan, H. Sun, S. Zhang, X. Li, Inorg. Chim. Acta 439 (2016) 100 (https://doi.org/10.1016/j.ica.2015.10.006)

D. J. Abrams, J. G. West, E. J. Sorensen, Chem. Sci. 8 (2017) 1954 (https://doi.org/10.1039/C6SC04607J)

H. Alawisi, K. F. Al-Afyouni, H. D. Arman, Z. J. Tonzetich, Organometallics 37 (2018) 4128 (https://doi.org/10.1021/acs.organomet.8b00668)

30. D. Kolb, M. Morgenstern, B. König, Chem. Commun. 59 (2023) 8592 (https://doi.org/10.1039/D3CC02170J)

D. Kolb, A. A. Almasalma, M. Morgenstern, L. Ganser, I. Weidacher, B. König, ChemPhotoChem 7 (2023) e202300167 (https://doi.org/10.1002/cptc.202300167)

A. Dobbs, J. Org. Chem. 66 (2001) 638 (https://doi.org/10.1021/jo0057396)

A. Ramanathan, L. S. Jimenez, Synthesis (2010) 217 (https://doi.org/10.1055/s-0029-1217112)

S. Agarwal, S. R. Al-Abed, D. D. Dionysiou, Environ. Sci. Technol. 41 (2007) 3722 (https://doi.org/10.1021/es062886y)

A. Kokanović, V. Ajdačić, N. Terzić Jovanović, S. Stankic, I. M. Opsenica, ACS Appl. Nano Mater. 6 (2023) 15820 (https://doi.org/10.1021/acsanm.3c02743)

J. Li, T. Zheng, H. Suna, X. Li, Dalton Trans. 42 (2013) 13048 (https://doi.org/10.1039/C3DT50409C)

K. S. Chan, C. R. Liu, K. L. Wong, Tetrahedron Lett. 56 (2015) 2728 (https://doi.org/10.1016/j.tetlet.2015.04.014)

C. Chen, H. Zuo, K. S. Chan, Tetrahedron 75 (2019) 510 (https://doi.org/10.1016/j.tet.2018.12.010)

R. Z. Liao, S. L. Chen, P. E. M. Siegbahn, ACS Catal. 5 (2015) 7350 (https://doi.org/10.1021/acscatal.5b01502)

B. Sahoo, A. E. Surkus, M. M. Pohl, J. Radnik, M. Schneider, S. Bachmann, M. Scalone, K. Junge, M. Beller, Angew. Chem. Int. Ed. 56 (2017) 11242 (https://doi.org/10.1002/anie.201702478)

B. R. P. Reddy, A. Auffrant, C. Gosmini, Asian J. Org. Chem. 10 (2021) 3275 (https://doi.org/10.1002/ajoc.202100616)

K. M. McCauley, D. A. Pratt, S. R. Wilson, J. Shey, T. J. Burkey, W. A. van der Donk, J. Am. Chem. Soc. 127 (2005) 1126 (https://doi.org/10.1021/ja048573p)

43. H. Shimakoshi, M. Tokunaga, T. Babaa, Y. Hisaeda, Chem. Commun. (2004) 1806 (https://doi.org/10.1039/B406400C)

H. Shimakoshi, Y. Hisaeda, Chem. Rec. 21 (2021) 2080 (https://doi.org/10.1002/tcr.202100077)

H. Shimakoshi, Y. Hisaeda, ChemPlusChem 82 (2017) 18 (https://doi.org/10.1002/cplu.201600303)

J. M. Herrmann, B. König, Eur. J. Org. Chem. (2013) 7017 (https://doi.org/10.1002/ejoc.201300657)

M. Tobisu, K. Yamakawa, T. Shimasakia, N. Chatani, Chem. Commun. 47 (2011) 2946 (https://doi.org/10.1039/C0CC05169A)

T. Funabiki, Y. Yamazaki, K. Tarama, J. Chem. Soc., Chem. Commun. (1978) 63 (https://doi.org/10.1039/C39780000063)

J. T. Lee, H. Alper, Tetrahedron Lett. 31 (1990) 4101 (https://doi.org/10.1016/S0040-4039(00)97553-1)

B. H. Gross, R. C. Mebane, D. L. Armstrong, Appl. Catal., A 219 (2001) 281 (https://doi.org/10.1016/S0926-860X(01)00700-1)

Y. L. Ren, M. Tian, X. Z. Tian, Q. Wang, H. Shang, J. Wang, Z. C. Zhang, Catal. Commun. 52 (2014) 36 (https://doi.org/10.1016/j.catcom.2014.03.036)

J. Fukuda, K. Nogi, H. Yorimitsu, Asian J. Org. Chem. 7 (2018) 2049 (https://doi.org/10.1002/ajoc.201800473).

Cobalt catalyzed defunctionalization reactions Review article