2‐Arylbenzyl Methyl Ethers as Precursors for the Tandem Synthesis of Benzo[c]coumarins Over Heterogeneous Visible‐Light Photoredox Catalysis with Graphitic Carbon Nitride (g‐C3N4). Issue 2 (4th January 2023)

• Record Type: Journal Article
• Authors: Natarajan, Palani; Pooja, ; Meena,
• Is Part Of: Asian journal of organic chemistry. Volume 12:Issue 2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-04
• Subjects: aqueous medium -- heterogeneous photocatalyst -- multiple C−H functionalization -- three reactions in one-pot -- transition metal-free -- waste to wealth; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200643
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Utilizing readily accessible 2‐arylbenzyl methyl ethers as precursors, an unprecedented three reactions in one‐pot protocol for the synthesis of benzo[ c ]coumarins over heterogeneous visible‐light photoredox catalysis with graphitic carbon nitride (g‐C3 N4 ) has been developed. Also, a possible reaction mechanism has been explored. Upon irradiation, g‐C3 N4 converts molecular oxygen into superoxide radical anion, which facilitates the benzylic oxidation of 2‐arylbenzyl methyl ethers into methyl [1, 1′‐biaryl]‐2‐carboxylate. The required benzo[ c ]coumarins are then produced through the hydrolysis and dehydrogenative lactonization of methyl [1, 1′‐biaryl]‐2‐carboxylate. The main attributes of this transformation include mildness, convenience in catalyst recovery and reuse, compatibility with lithium persulfate produced from the spent lithium‐ion batteries, works in aqueous medium, and is a multiple C−H functionalization processes happen via three reactions (oxidation, hydrolysis and dehydrogenative lactonization) in one‐pot at ambient conditions. Abstract : With readily accessible 2‐arylbenzyl methyl ethers as precursors, three reactions in one‐pot protocol for the synthesis of benzo[ c ]coumarins over heterogeneous visible‐light photoredox catalysis with graphitic carbon nitride is described. This method functions in an aqueous media and is compatible with waste‐derived persulfate.