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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of
Forough Nasuhipur1, Zarrin Ghasemi1, Morgane Poupon2
1Department of Organic Chemistry and Biochemistry, Faculty of Chemistry, University of Tabriz Tabriz 5166614766 Iran z.ghasemi@tabrizu.ac.ir.
Abstract:
A class of indenopyrroles is presented by the treatment of known dihydroxy-2-methyl-4-oxoindeno[1,2-b]pyrroles with phosphorus oxychloride (POCl3). The elimination of vicinal hydroxyl groups at the 3a and 8b positions, formation of a π bond, and electrophilic chlorination of the methyl group attached to C2 resulted in the fused aromatic pyrrole structures. Benzylic substitution of various nucleophiles such as H2O, EtOH, and NaN3 with a chlorine atom gave diverse 4-oxoindeno[1,2-b]pyrrole derivatives in 58 to 93% yields. The reaction was investigated in different aprotic solvents, and the highest reaction yield was obtained in DMF. The structures of the products were confirmed by spectroscopic methods, elemental analysis, and X-ray crystallography.
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