The synthesis of 1,4-dicarbonyl systems is more challenging and less easily conceptualized. 1,4-Dicarbonyl compounds serve as building blocks for natural products and biological molecules, and as valuable precursors for constructing five-membered heterocycles such as pyrrole, furan, and thiophene.2 These units are key in medicinal chemistry, food chemistry, and polymer science.1 The strategies for synthesizing 1,4-dicarbonyl scaffolds are categorized into two types: i) bond formation between the carbonyl-containing fragments and ii) transformation or coupling of non-carbonyl precursors to yield the carbonyls on reaction. In this seminar, I will follow various retrosynthesis routes and describe the synthesis of the 1,4-dicarbonyl frameworks involving Stetter-type reaction,3 oxidative coupling with enolonium-type reaction,4 and so on. Besides, I will also discuss the formation of 2,3-benzo-fused 1,4-diketones via C‒H acylation5 and oxidative ring-opening of heteroaromatics.6 In my research proposal, I will present our efforts in developing 9,10-diaroylphenanthrene derivatives from arylated thiophenes employing a photocatalyst-free method under UV light and aerobic conditions.

References:
1) Igau, A.; Grutzmacher, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc., 1988, 110, 6463–6466.
2) Khaghaninejad, S.; Heravi, M. M. In Adv. Heterocycl. Chem., 2014, 111, 95-146.
3) Stetter. H. Angew. Chem. Int. Ed. 1976, 15, 639–647.
4) Parida, K. N.; Pathe, G. K.; Maksymenko, S.; Szpilman, A. M. Beilstein J. Org. Chem. 2018, 14, 992–997.
5) Lee, P. Y.; Liang, P.; Yu, W. Y. Org. Lett. 2017, 19, 2082–2085.
6) Meganathan, N.; Ramakrishnan, S.; Arasambattu, K. M. Eur. J. Org. Chem. 2012, 3647–3657.