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Abstract

An investigation towards 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)-catalyzed cross-dehydrogenative coupling (CDC) reactions of trans-3-phenylthio/benzylthioazetidin-2-ones (1a,b) and ethyl-2- phenylthioethanoates (5) with aliphatic/aromatic nucleophiles is described. A series of reaction conditions were chosen to obtain the monosubstituted and disubstituted β-lactams. However, CDC reactions of β-lactams with different aliphatic/aromatic substrates resulted into unidentified products whereas ethyl-2-phenylthioethanoates (5) underwent the CDC reaction to give the desired α-substituted ethyl- 2-phenylthioethanoates (7). Also, a plausible mechanism for the cross coupling of ethyl-2-phenylthioethanoates (5) with nucleophiles is described.

Keywords

Cross-dehydrogenative coupling C-H activation Copper catalyst Nucleophile Oxidation b-Lactams

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Narula, D., S. Bari, S., K. Banik, B., & Bhalla, A. (2017). An Investigation Towards 2,3-Dichloro- 5,6-dicyanobenzoquinone Catalyzed Cross- Dehydrogenative Coupling Reactions of Thio-β-lactams/Thioethanoates with Aliphatic/Aromatic Nucleophiles. Asian Journal of Organic & Medicinal Chemistry, 2(2), 58–62. https://doi.org/10.14233/ajomc.2017.AJOMC-P35
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