Site-Selective Ruthenium-Catalyzed C-H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

The Journal of Organic Chemistry
Yu-Chao YuanRafael Gramage-Doria

Abstract

Biologically relevant N-arylisoindolinones efficiently underwent arylation reactions under ruthenium catalysis via C-H bond functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily available and benchmark stable boronic acid and potassium aryltrifluoroborate derivatives as coupling partners. An appealing late-stage functionalization of indoprofen applying this methodology is showcased.

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Citations

Jan 15, 2021·The Journal of Organic Chemistry·Peng-Peng NiuYu-Peng He
Apr 14, 2021·Chemistry : a European Journal·Sunil Kumar Sunnam, Jitendra D Belani
Oct 31, 2020·Journal of the American Chemical Society·Jyoti DhankharIlija Čorić
Nov 26, 2019·The Journal of Organic Chemistry·Yu-Chao YuanRafael Gramage-Doria
Oct 19, 2019·The Journal of Organic Chemistry·Jonathan A EllmanBing-Feng Shi
Jan 7, 2020·The Journal of Organic Chemistry·Kunyoung KimIn Su Kim
Mar 28, 2020·The Journal of Organic Chemistry·Krista Gulbe, Māris Turks

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