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Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1403-1413

http://dx.doi.org/10.1351/PAC-CON-09-08-17

Published online 2010-05-02

Transition-metal-catalyzed direct arylations via C–H bond cleavages

Lutz Ackermann

Institute of Organic and Biomolecular Chemistry, Georg-August‑Universität, Tammannstrasse 2, 37077 Göttingen (Germany)

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  • Kornhaaß Christoph, Kuper Christian, Ackermann Lutz: Ferrocenylalkynes for Ruthenium-Catalyzed Isohypsic CH/NO Bond Functionalizations. Adv. Synth. Catal. 2014, n/a. <http://dx.doi.org/10.1002/adsc.201301156>
  • Li Jie, John Michael, Ackermann Lutz: Amidines for Versatile Ruthenium(II)-Catalyzed Oxidative CH Activations with Internal Alkynes and Acrylates. Chem. Eur. J. 2014, n/a. <http://dx.doi.org/10.1002/chem.201304944>
  • Nakanowatari Sachiyo, Ackermann Lutz: Ruthenium(II)-Catalyzed Synthesis of Isochromenes by CH Activation with Weakly Coordinating Aliphatic Hydroxyl Groups. Chem. Eur. J. 2014, n/a. <http://dx.doi.org/10.1002/chem.201400161>
  • Aparna P.S., Prabha B., Prakash Praveen, Jijy E., Luxmi Varma R., Radhakrishnan K.V.: Ruthenium catalyzed desymmetrization of diazabicyclic olefins to access heteroaryl substituted cyclopentenes through C–H activation of phenylazoles. Tetrahedron Letters 2014, 55, 865. <http://dx.doi.org/10.1016/j.tetlet.2013.12.029>
  • Schinkel Marvin, Wang Lianhui, Bielefeld Kris, Ackermann Lutz: Ruthenium(II)-Catalyzed C(sp3)–H α-Alkylation of Pyrrolidines. Org. Lett. 2014, 16, 1876. <http://dx.doi.org/10.1021/ol500300w>
  • Thirunavukkarasu Vedhagiri S., Kozhushkov Sergei I., Ackermann Lutz: C–H nitrogenation and oxygenation by ruthenium catalysis. Chem. Commun. 2014, 50, 29. <http://dx.doi.org/10.1039/c3cc47028h>
  • Liu Weiping, Ackermann Lutz: Versatile ruthenium(ii)-catalyzed C–H cyanations of benzamides. Chem. Commun. 2014, 50, 1878. <http://dx.doi.org/10.1039/c3cc49502g>
  • Liu Wei, Li Yahui, Wang Yue, Kuang Chunxiang: Site-Selective Direct Arylation of 1,2,3-Triazole N -Oxides. Eur. J. Org. Chem. 2013, 2013, 5272. <http://dx.doi.org/10.1002/ejoc.201300747>
  • Diers Emelyne, Phani Kumar N.Y., Mejuch Tom, Marek Ilan, Ackermann Lutz: Carboxylate-assisted ruthenium(II)-catalyzed C–H arylations of 5-aryl tetrazoles: step-economical access to Valsartan. Tetrahedron 2013, 69, 4445. <http://dx.doi.org/10.1016/j.tet.2013.01.006>
  • Hofmann Nora, Ackermann Lutz: meta-Selective C–H Bond Alkylation with Secondary Alkyl Halides. J. Am. Chem. Soc. 2013, 135, 5877. <http://dx.doi.org/10.1021/ja401466y>
  • Wang Lianhui, Ackermann Lutz: Versatile Pyrrole Synthesis through Ruthenium(II)-Catalyzed Alkene C–H Bond Functionalization on Enamines. Org. Lett. 2013, 15, 176. <http://dx.doi.org/10.1021/ol303224e>
  • Yang Fanzhi, Ackermann Lutz: Ruthenium-Catalyzed C–H Oxygenation on Aryl Weinreb Amides. Org. Lett. 2013, 15, 718. <http://dx.doi.org/10.1021/ol303520h>
  • Yadav M. Ramu, Rit Raja K., Sahoo Akhila K.: Sulfoximine Directed Intermolecular o-C–H Amidation of Arenes with Sulfonyl Azides. Org. Lett. 2013, 15, 1638. <http://dx.doi.org/10.1021/ol400411v>
  • Liu Weiping, Ackermann Lutz: Ortho- and Para-Selective Ruthenium-Catalyzed C(sp2)–H Oxygenations of Phenol Derivatives. Org. Lett. 2013, 15, 3484. <http://dx.doi.org/10.1021/ol401535k>
  • Kozhushkov Sergei I., Potukuchi Harish Kumar, Ackermann Lutz: Direct C–H bond arylations and alkenylations with phenol-derived fluorine-free electrophiles. Catal. Sci. Technol. 2013, 3, 562. <http://dx.doi.org/10.1039/c2cy20505j>
  • Kozhushkov Sergei I., Ackermann Lutz: Ruthenium-catalyzed direct oxidative alkenylation of arenes through twofold C–H bond functionalization. Chem. Sci. 2013, 4, 886. <http://dx.doi.org/10.1039/c2sc21524a>
  • Shan Gang, Han Xuesong, Lin Yun, Yu Shanyou, Rao Yu: Broadening the catalyst and reaction scope of regio- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis. Org. Biomol. Chem. 2013, 11, 2318. <http://dx.doi.org/10.1039/c3ob27457h>
  • Ackermann Lutz, Mehta Vaibhav P.: Palladium-Catalyzed Mono-α-Arylation of Acetone with Aryl Imidazolylsulfonates. Chem. Eur. J. 2012, 18, 10230. <http://dx.doi.org/10.1002/chem.201201394>
  • Hu Yimin, Zhu Tao, Mu Xiaolong, Zhao Quansheng, Yu Tao, Wen Lei, Zhang Yulong, Wu Min, Zhang Hao: Synthesis of highly substituted dihydropyrrolophenanthridine derivatives by tandem reaction. Tetrahedron 2012, 68, 311. <http://dx.doi.org/10.1016/j.tet.2011.10.041>
  • Kornhaaß Christoph, Li Jie, Ackermann Lutz: Cationic Ruthenium Catalysts for Alkyne Annulations with Oximes by C–H/N–O Functionalizations. J. Org. Chem. 2012, 77, 9190. <http://dx.doi.org/10.1021/jo301768b>
  • Ackermann Lutz, Lygin Alexander V.: Cationic Ruthenium(II) Catalysts for Oxidative C–H/N–H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water. Org Lett 2012, 14, 764. <http://dx.doi.org/10.1021/ol203309y>
  • Ackermann Lutz, Diers Emelyne, Manvar Atul: Ruthenium-Catalyzed C–H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles. Org Lett 2012, 14, 1154. <http://dx.doi.org/10.1021/ol3000876>
  • Zhao He, Wang Ruifang, Chen Ping, Gregg Brian T., Hsia Ming Min, Zhang Wei: Palladium-Catalyzed Direct Arylation of Imidazolone N-Oxides with Aryl Bromides and Its Application in the Synthesis of GSK2137305. Z Org Lett 2012, 14, 1872. <http://dx.doi.org/10.1021/ol300468g>
  • Ackermann Lutz, Kornhaass Christoph, Zhu Yingjun: Palladium-Catalyzed Direct C–H Bond Alkynylations of Heteroarenes Using gem-Dichloroalkenes. Z Org Lett 2012, 14, 1824. <http://dx.doi.org/10.1021/ol300514d>
  • Ackermann Lutz, Pospech Jola, Potukuchi Harish Kumar: Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C–H/C–O Bond Arylations with Phenols in Water. Z Org Lett 2012, 14, 2146. <http://dx.doi.org/10.1021/ol300671y>
  • Yang Yiqing, Lin Yun, Rao Yu: Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group. Org. Lett. 2012, 120522105335003. <http://dx.doi.org/10.1021/ol301104n>
  • Thirunavukkarasu Vedhagiri S., Donati Margherita, Ackermann Lutz: Hydroxyl-Directed Ruthenium-Catalyzed C–H Bond Functionalization: Versatile Access to Fluorescent Pyrans. Org. Lett. 2012, 14, 3416. <http://dx.doi.org/10.1021/ol301387t>
  • Graczyk Karolina, Ma Wenbo, Ackermann Lutz: Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C–H Bond Cleavages. Org. Lett. 2012, 14, 4110. <http://dx.doi.org/10.1021/ol301759v>
  • Thirunavukkarasu Vedhagiri S., Hubrich Jonathan, Ackermann Lutz: Ruthenium-Catalyzed Oxidative C(sp2)–H Bond Hydroxylation: Site-Selective C–O Bond Formation on Benzamides. Org. Lett. 2012, 14, 4210. <http://dx.doi.org/10.1021/ol3018819>
  • Hu Jiantao, Chen Shi, Sun Yonghui, Yang Jing, Rao Yu: Synthesis of Tri- and Tetrasubstituted Pyrazoles via Ru(II) Catalysis: Intramolecular Aerobic Oxidative C–N Coupling. Org. Lett. 2012, 14, 5030. <http://dx.doi.org/10.1021/ol3022353>
  • Thirunavukkarasu Vedhagiri S., Ackermann Lutz: Ruthenium-Catalyzed C–H Bond Oxygenations with Weakly Coordinating Ketones. Org. Lett. 2012, 14, 6206. <http://dx.doi.org/10.1021/ol302956s>
  • Ma Wenbo, Graczyk Karolina, Ackermann Lutz: Ruthenium-Catalyzed Alkyne Annulations with Substituted 1H-Pyrazoles by C–H/N–H Bond Functionalizations. Org. Lett. 2012, 14, 6318. <http://dx.doi.org/10.1021/ol303083n>
  • Li Jie, Kornhaaß Christoph, Ackermann Lutz: Ruthenium-catalyzed oxidative C–H alkenylation of aryl carbamates. Chem. Commun. 2012, 48, 11343. <http://dx.doi.org/10.1039/c2cc36196e>
  • Ackermann Lutz, Punji Benudhar, Song Weifeng: User-Friendly [(Diglyme)NiBr2]-Catalyzed Direct Alkylations of Heteroarenes with Unactivated Alkyl Halides through CH Bond Cleavages. Synth Catal 2011, 353, 3325. <http://dx.doi.org/10.1002/adsc.201100487>
  • Hu Yimin, Sun Yongjie, Hu Jiping, Zhu Tao, Yu Tao, Zhao Quansheng: Fused Phenanthridines: Domino Cyclization of 1,6-Diynes with Bromo(iso)quinoline. Chem Asian J 2011, 6, 797. <http://dx.doi.org/10.1002/asia.201000692>
  • Ackermann Lutz, Kapdi Anant R., Fenner Sabine, Kornhaaß Christoph, Schulzke Carola: Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates. Chem Eur J 2011, 17, 2965. <http://dx.doi.org/10.1002/chem.201002386>
  • Christiansen Andrea, Selent Detlef, Spannenberg Anke, Köckerling Martin, Reinke Helmut, Baumann Wolfgang, Jiao Haijun, Franke Robert, Börner Armin: Heteroatom-Substituted Secondary Phosphine Oxides (HASPOs) as Decomposition Products and Preligands in Rhodium-Catalysed Hydroformylation. Chemistry A European Journal 2011, 17, 2120. <http://dx.doi.org/10.1002/chem.201002823>
  • Vasseur Alexandre, Muzart Jacques, Le Bras Jean: Dehydrogenative Heck Reaction of Furans and Thiophenes with Styrenes under Mild Conditions and Influence of the Oxidizing Agent on the Reaction Rate. Chemistry A European Journal 2011, 17, 12556. <http://dx.doi.org/10.1002/chem.201101992>
  • Ackermann Lutz: ChemInform Abstract: Transition Metal Catalyzed Direct Arylations via C-H Bond Cleavages. ChemInform 2011, 42, no. <http://dx.doi.org/10.1002/chin.201123225>
  • Rossi Renzo, Bellina Fabio, Lessi Marco: Highly selective palladium-catalyzed Suzuki–Miyaura monocoupling reactions of ethene and arene derivatives bearing two or more electrophilic sites. Tetrahed 2011, 67, 6969. <http://dx.doi.org/10.1016/j.tet.2011.06.001>
  • Meng Tuan-jie, Hu Yimin, Zhao Quansheng, Yu Tao, Wang Shaowu: Construction of 3-allylidene-4-vinyltetrahydrofurans and 3-allylidene-4-vinylpyrrolidines via sequential domino allylation/olefination of C–C triple bonds. Tedrahedron 2011, 67, 8710. <http://dx.doi.org/10.1016/j.tet.2011.09.026>
  • Ackermann Lutz, Dell’Acqua Monica, Fenner Sabine, Vicente Rubén, Sandmann René: Metal-Free Direct Arylations of Indoles and Pyrroles with Diaryliodonium Salts. Org Lett 2011, 13, 2358. <http://dx.doi.org/10.1021/ol200601e>
  • Ackermann Lutz, Barfüsser Sebastian, Kornhaass Christoph, Kapdi Anant R.: C–H Bond Arylations and Benzylations on Oxazol(in)es with a Palladium Catalyst of a Secondary Phosphine Oxide. Org Lett 2011, 13, 3082. <http://dx.doi.org/10.1021/ol200986x>
  • Ackermann Lutz, Lygin Alexander V.: Ruthenium-Catalyzed Direct C–H Bond Arylations of Heteroarenes. Org Lett 2011, 13, 3332. <http://dx.doi.org/10.1021/ol2010648>
  • Ackermann Lutz, Lygin Alexander V., Hofmann Nora: Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C–H/N–H Bond Functionalizations. Org Lett 2011, 13, 3278. <http://dx.doi.org/10.1021/ol201244s>
  • 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>
  • Ackermann Lutz: Air-Stable Bifunctional HASPO Preligands for Metal-Catalyzed Cross-Couplings and Direct C-H Bond Arylations. Isr J Chem 2010, 50, 652. <http://dx.doi.org/10.1002/ijch.201000043>