Regioselective Synthesis of Polycyclic and Heptagon‐embedded Aromatic Compounds through a Versatile π‐Extension of Aryl Halides. Issue 25 (16th May 2017)

• Record Type: Journal Article
• Authors: Fu, Wai Chung; Wang, Zheng; Chan, Wesley Ting Kwok; Lin, Zhenyang; Kwong, Fuk Yee
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 25(2017)
• Page Start: 7166
• Page End: 7170
• Publication Date: 2017-05-16
• Subjects: C−H functionalization -- cross-coupling -- decarboxylation -- palladium -- polycyclic aromatic hydrocarbons; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201703551
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A versatile π‐extension reaction was developed based on the three‐component cross‐coupling of aryl halides, 2‐haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho ‐C−H activator and ethylene synthon via a retro‐Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates. Abstract : Another slice of pi : A versatile π‐extension reaction was developed based on the three‐component cross‐coupling of aryl halides, 2‐haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxy group, while norbornadiene serves as an ortho ‐C−H activator and ethylene synthon via a retro‐Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.