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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1127-1134

http://dx.doi.org/10.1351/pac200880051127

Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes and alkenes

Tetsuya Satoh, Kenji Ueura and Masahiro Miura

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

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  • Ackermann Lutz, Pospech Jola, Graczyk Karolina, Rauch Karsten: Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C–H/O–H Bond Cleavages. Org Lett 2012, 14, 930. <http://dx.doi.org/10.1021/ol2034614>
  • Zhu Yanjun, Smith Dan A., Herbert David E., Gatard Sylvain, Ozerov Oleg V.: C–H and C–O oxidative addition in reactions of aryl carboxylates with a PNP pincer-ligated Rh(i) fragment. Chem Commn 2012, 48, 218. <http://dx.doi.org/10.1039/c1cc15845g>
  • Hashimoto Yuto, Ortloff Timon, Hirano Koji, Satoh Tetsuya, Bolm Carsten, Miura Masahiro: Ru/Ag-Catalyzed Oxidative Alkenylation of Benzamides and Phenylazoles through Regioselective C–H Bond Cleavage. Chem Lett (Japan) 2012, 41, 151. <http://dx.doi.org/10.1246/cl.2012.151>
  • Omae Iwao: Transition metal-catalyzed cyclocarbonylation in organic synthesis. Coord Chem Rev - 2011, 255, 139. <http://dx.doi.org/10.1016/j.ccr.2010.08.001>
  • Ackermann Lutz, Pospech Jola: Ruthenium-Catalyzed Oxidative C–H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones. Org Lett 2011, 13, 4153. <http://dx.doi.org/10.1021/ol201563r>
  • Wei Xiaohong, Zhao Miao, Du Zhengyin, Li Xingwei: Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed Oxidative Coupling. Org Lett 2011, 13, 4636. <http://dx.doi.org/10.1021/ol2018505>
  • Wrigglesworth Joe W., Cox Brian, Lloyd-Jones Guy C., Booker-Milburn Kevin I.: New Heteroannulation Reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C–H Activation. Org Lett 2011, 13, 5326. <http://dx.doi.org/10.1021/ol202187h>
  • Hashimoto Yuto, Ueyama Takumi, Fukutani Tatsuya, Hirano Koji, Satoh Tetsuya, Miura Masahiro: Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C–H Bond Cleavage Directed by a Nitrogen-containing Group. Chem Lett (Japan) 2011, 40, 1165. <http://dx.doi.org/10.1246/cl.2011.1165>
  • Mochida Satoshi, Shimizu Masaki, Hirano Koji, Satoh Tetsuya, Miura Masahiro: Synthesis of Naphtho[1,8-bc]pyran Derivatives and Related Compounds through Hydroxy Group Directed CH Bond Cleavage under Rhodium Catalysis. Chem Asian J 2010, 5, 847. <http://dx.doi.org/10.1002/asia.200900639>
  • Chen Shuo-Ping, Zhao Pinjing, Sun Zhong-Ming: Tertiary Carbinamine Synthesis by Rhodium-Catalyzed [3+2] Annulation of N-Unsubstituted Aromatic Ketimines and Alkynes. Chem Eur J 2010, 16, 2619. <http://dx.doi.org/10.1002/chem.200902814>
  • Satoh Tetsuya, Miura Masahiro: Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis. Chem Eur J 2010, 16, 11212. <http://dx.doi.org/10.1002/chem.201001363>
  • Iwai Tomohiro, Fujihara Tetsuaki, Terao Jun, Tsuji Yasushi: Iridium-Catalyzed Annulation of N-Arylcarbamoyl Chlorides with Internal Alkynes. J Am Chem Soc 2010, 132, 9602. <http://dx.doi.org/10.1021/ja104153k>
  • Wagner Christoph, Gómez-Ruiz Santiago, Steinborn Dirk, Block Michael: Synthesis, characterization and structures of cyclic organorhodium complexes of the type [Rh{CH(SO2Ph)CH2CH2YR2-κC,κY}L2] (YR2 = PPh2, NMe2; L2 = diphosphine, cyclooctadiene). Dalton Trans 2010, 39, 4636. <http://dx.doi.org/10.1039/c001452d>
  • Fukutani Tatsuya, Umeda Nobuyoshi, Hirano Koji, Satoh Tetsuya, Miura Masahiro: Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C–H bond cleavage. Chem Commun 2009, 5141. <http://dx.doi.org/10.1039/b910198e>
  • El Sawy Ehab N., Birss Viola I.: Nano-porous iridium and iridium oxide thin films formed by high efficiency electrodeposition. J Mater Chem 2009, 19, 8244. <http://dx.doi.org/10.1039/b914662h>
  • Satoh Tetsuya, Ueura Kenji, Miura Masahiro: ChemInform Abstract: Rhodium- and Iridium-Catalyzed Oxidative Coupling of Benzoic Acids with Alkynes and Alkenes. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200842264>