Utility of iodine catalyzed tandem oxidation, cross-coupling and cyclisation reactions in organic synthesis

Keywords: Cross coupling, cyclisation, Oxidation

Abstract

Molecular iodine is an eco-friendly, powerful catalyst and plays an important role in pharmaceutical, medicinal and organic chemistry. For a long time, molecular iodine has been hugely applied in carbohydrate chemistry. Due to the huge application of molecular iodine in oxidation, cross coupling and cyclisation reactions, it has emerged as an elegant tool in organic synthesis. Earlier I discussed (Biswas, 2021) on iodine mediated cascade oxidative functionalisation, cyclisation and annulation reactions. In this review, I describe the utility of iodine catalysed tandem oxidation, cross coupling, and cyclisation reactions in organic synthesis. Molecular iodine catalysed mild oxidative conditions yielding desired products, and oxidising techniques applied to the efficient synthesis tolerate a wide range of starting materials with aryl or alkyl replacements. These reactions were carried out as a one-pot or multi-step eco-friendly process that could be used for a wide range of drug and pharmaceutical product synthesis.

References

Biswas, T. (2021). Iodine mediated cascade oxidative functio-nalization, cyclisation and annulation reactions. Int. J. Exp. Res. Rev. 25: 57-65.

Cai, Q., Zhu, Y. P., Gao, Y., Sun, J. J., & Wu, A. X. (2013). A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives. Can. J. Chem. 91: 414-419.

Cao, L., Ding, J., Gao, M., Wang, Z., Juan Li, J., & Anxin, Wu, A. (2009). Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia. Org. Lett. 11 (17): 3810-3813.

Chen, Z., Li, H., Dong, W., Miao, M., & Ren, H. (2016). I2‑Catalyzed Oxidative Coupling Reactions of Hydra-zones and Amines and the Application in the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles. Org. Lett. 18(6): 1334–1337.

Devari, S., Kumar, A., Deshidi, R., & Shah, B. A. (2015). C-H Functionalization of Terminal Alkynes Towards Ste-reospecific Synthesis of (E) or (Z) 2- Methylthio-1,4-ene-diones. Chem. Commun. 51: 5013.

Gao, M., Yin, G., Wang, Z., Wu, Y., Guo, C., Pan, Y., & Wu, A. (2009). A concise and efficient way to synthesize po-lyenicdiones directly from α,β-unsaturated methyl ke-tones. Tetrahedron. 65: 6047-6049.

Gao, Q., Wu, X., Liu, S., & Wu, A. (2014). I2‑Promoted Se-lective Oxidative Cross-Coupling/Annulation of 2‑Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1‑b] furan-1(2H)‑ones with a Quaternary Center. Org. Lett. 16: 1732−1735.

Kalmode, H. P., Kamlesh S. Vadagaonkar, K. S., & Atul C. Chaskar, A. C. (2014). Metal-free in situ sp3, sp2, and sp C–H functionalization and oxidative cross-coupling with benzamidines hydrochloride: a promising approach for the synthesis of α-ketoimides. RSC Adv. 4: 60316-60326.

Li, X., Mao, Z., Wang, Y., Chen, W., & Lin, X. (2011). Mole-cular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three component reaction of amines, aldehydes, and alkynes. Tetrahedron. 67: 3858-3862.

Liu, J. M., Liu, X. Y., Qing, X. S., Wang, T., & Wang, C. D. (2017). I2/K2CO3-promoted ring-opening / cyclization / rearrangement / aromatization sequence: A powerful strategy for the synthesis of polysubstituted furans. Chin. Chem. Lett. 28 (2): 458-462.

Patil, S. V., Patil, S. S., & Bobade, V. D. (2016). A simple and efficient approach to the synthesis of 2-substituted ben-zimidazole via sp3 C-H functionalization. Arabian Journal of Chemistry. 9: S515-S521.

Ramesha, B. A., Kumar, C. S. P., Sandhya, N. C., Kumara, N. M., Mantelingu, K., & Rangappa, S. K. (2016). Tandem Approachl for the Synthesis of 3-Sulfenylimidazo[1,5-a]pyridines from Dithioesters. RSC Adv. 54:1-5.

Sun, J., Qiu, J. K., Jiang, B., Wen-Juan Hao, W. J., Guo, C., & Tu, S. J. (2016). I2-Catalyzed Multicomponent Reac-tions for Accessing Densely Functionalized Pyrazo-lo[1,5-a]pyrimidines and Their Disulphenylated Deriva-tives. J. Org. Chem. 81(8): 3321–3328.

Vadagaonkar, K., Kalmode, H., Murugan, K., & Chaskar, A. (2014). I2 Catalyzed Tandem Protocol for Synthesis of Quinoxalines via sp3, sp2 and sp C-H Functionalization. RSC Adv. 5(8): 5080-5590.

Xu, H. Y., Xu, X. P., Wang, S. Y., & Shun-Jun Ji, S. J. (2012). Synthesis of Indeno[1,2-b]indole Derivatives through One-Pot Sequential or Two-Step Iodine-Catalyzed C–O Activation and Palladium-Catalyzed C–H Functionali-zation. Eur. J. Org. Chem. 2012: 28.

Yang, Y., Gao, M., Shu, W. M., Wu, L. M., Zhang, D. X., & Wu, A. X. (2013). Synthesis of α-iodoketals from methyl ketones via sustainable and orthogonal tandem ca-talysis. Org. Biomol. Chem. 11: 1226-1233.

Zhu, Y. P., Yuan, J. J., Zhao, Q., Gao, M. Q. H., Liu, M. C., Yang, Y., & Wu, A. X. (2012). I2/CuO-catalyzed tan-dem cyclization strategy for one-pot synthesis of substi-tuted 2-aminothiozole from easily available aromatic ketones/a,b-unsaturated ketones and thiourea. Tetrahe-dron. 68: 173-178.

Published
2022-04-30
How to Cite
Biswas, T., & Biswas, S. (2022). Utility of iodine catalyzed tandem oxidation, cross-coupling and cyclisation reactions in organic synthesis. International Journal of Experimental Research and Review, 27, 39-44. https://doi.org/10.52756/ijerr.2022.v27.004
Section
Articles