RhIII-Catalyzed C−H Olefination of Benzoic Acids under Mild Conditions using Oxygen as the Sole Oxidant
作者： Quandi Jiang , Changlei Zhu , Huaiqing Zhao , Weiping Su
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摘要: Phthalide skeletons have been synthesized for the first time through a Rh(III) -catalyzed C-H olefination of benzoic acids under mild conditions using oxygen as sole oxidant. Aromatic bearing variety functional groups could react with diverse alkenes to afford desired cyclized lactones or uncyclized alkenylarenes in moderate-to-excellent yields.
sci-hub.se 参考文章(59)
S. S. Stahl, Palladium-Catalyzed Oxidation of Organic Chemicals with O2 Science. ,vol. 309, pp. 1824- 1826 ,(2005) , 10.1126/SCIENCE.1114666
Vincent Ritleng, Claude Sirlin, Michel Pfeffer, Ru-, Rh-, and Pd-Catalyzed C-C Bond Formation Involving C-H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects Chemical Reviews. ,vol. 102, pp. 1731- 1770 ,(2002) , 10.1021/CR0104330
Huaiqing Zhao, Yaping Shang, Weiping Su, Rhodium(III)-catalyzed intermolecular N-chelator-directed aromatic C-H amidation with amides Organic Letters. ,vol. 15, pp. 5106- 5109 ,(2013) , 10.1021/OL4024776
Keary M. Engle, Dong-Hui Wang, Jin-Quan Yu, Constructing Multiply Substituted Arenes Using Sequential Palladium(II)‐Catalyzed C ? H Olefination Angewandte Chemie. ,vol. 49, pp. 6169- 6173 ,(2010) , 10.1002/ANIE.201002077
B. Ye, N. Cramer, Chiral Cyclopentadienyl Ligands as Stereocontrolling Element in Asymmetric C–H Functionalization Science. ,vol. 338, pp. 504- 506 ,(2012) , 10.1126/SCIENCE.1226938
Nicholas D. Ball, Jeff W. Kampf, Melanie S. Sanford, Aryl−CF3 Bond-Forming Reductive Elimination from Palladium(IV) Journal of the American Chemical Society. ,vol. 132, pp. 2878- 2879 ,(2010) , 10.1021/JA100955X
Marion H. Emmert, Amanda K. Cook, Yushu J. Xie, Melanie S. Sanford, Remarkably High Reactivity of Pd(OAc)2/Pyridine Catalysts: Nondirected CH Oxygenation of Arenes† Angewandte Chemie. ,vol. 50, pp. 9409- 9412 ,(2011) , 10.1002/ANIE.201103327
Baoqing Liu, Yang Fan, Yang Gao, Chao Sun, Cheng Xu, Jin Zhu, Rhodium(III)-catalyzed N-nitroso-directed C-H olefination of arenes. High-yield, versatile coupling under mild conditions. Journal of the American Chemical Society. ,vol. 135, pp. 468- 473 ,(2013) , 10.1021/JA3099245
Xi-Sha Zhang, Qi-Lei Zhu, Yun-Fei Zhang, Yan-Bang Li, Zhang-Jie Shi, Controllable Mono‐/Dialkenylation of Benzyl Thioethers through Rh‐Catalyzed Aryl C ? H Activation Chemistry: A European Journal. ,vol. 19, pp. 11898- 11903 ,(2013) , 10.1002/CHEM.201300829
Hua Yang, Gao-Yun Hu, Jun Chen, Yi Wang, Zhong-Hua Wang, Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone Bioorganic & Medicinal Chemistry Letters. ,vol. 17, pp. 5210- 5213 ,(2007) , 10.1016/J.BMCL.2007.06.082