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Deoxygenative Arylation of Carboxylic Acids by Aryl Migration |
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| Authors: | Rehanguli Ruzi Junyang Ma Prof. Dr. Xiang-Ai Yuan Wenliang Wang Shanshan Wang Dr. Muliang Zhang Dr. Jie Dai Prof. Dr. Jin Xie Prof. Dr. Chengjian Zhu |
| Affiliation: | 1. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Nanjing, University, Nanjing, 210023 P. R. China These authors contributed equally to this work.;2. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165 P. R. China These authors contributed equally to this work.;3. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, National Demonstration Center for Experimental Chemistry Education, School of Chemistry and Chemical Engineering, Nanjing, University, Nanjing, 210023 P. R. China;4. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165 P. R. China |
| Abstract: | An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C−O bond and formation of a weaker C−C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields. |
| Keywords: | aryl migration carboxylic acids deoxygenation ketones synergistic catalysis |