Palladium(II)‐Catalyzed Tandem Synthesis of Acenes Using Carboxylic Acids as Traceless Directing Groups. Issue 30 (31st May 2016)

• Record Type: Journal Article
• Authors: Kim, Kiho; Vasu, Dhananjayan; Im, Honggu; Hong, Sungwoo
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 30(2016)
• Page Start: 8652
• Page End: 8655
• Publication Date: 2016-05-31
• Subjects: acenes -- C-H functionalization -- decarboxylation -- palladium -- tandem reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201603661
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A straightforward synthetic strategy for generating useful anthracene derivatives was developed involving palladium(II)‐catalyzed tandem transformation with carboxylic acids as traceless directing groups. Carboxyl‐directed C‐H alkenylation, carboxyl‐directed secondary C‐H activation and rollover, intramolecular C−C bond formation, and decarboxylative aromatization are proposed as the key steps in the tandem reaction pathway. This novel synthetic route utilizes a broad range of substrates and provides a convenient synthetic tool that allows access to acenes. Abstract : Driving tandem : A tandem strategy that generates useful anthracene derivatives involves carboxy‐directed C‐H alkenylation and secondary C‐H activation, followed by rollover/intramolecular C−C bond formation/decarboxylative aromatization sequences. The synthetic route accommodates a broad range of substrates and their acene products.