One of the simplest and most utilised chemical reactions is the burning of hydrocarbons and while combustion is an excellent way to exploit the energy content of this naturally occurring resource, there is a lot more we can do with the ‘inert’ C-H bond.
C-H activation allows us to convert cheaper hydrocarbon starting materials into more valuable and versatile products; leading to the development of a wide range of reagents and catalysts that activate C-H bonds. To keep you up to date with the latest developments in the field we have created this article collection, where all articles are free to download until 15th December.
Investigating N-methoxy-N′-aryl ureas in oxidative C–H olefination reactions: an unexpected oxidation behaviour, Jens Willwacher, Souvik Rakshit and Frank Glorius, Org. Biomol. Chem., 2011, 9, 4736-4740
Greener solvents for ruthenium and palladium-catalysed aromatic C–H bond functionalisation, Cedric Fischmeister and Henri Doucet, Green Chem., 2011, 13, 741-753
1,5-Migration of rhodium via C–H bond activation in catalytic decyanative silylation of nitriles, Mamoru Tobisu, Junya Hasegawa, Yusuke Kita, Hirotaka Kinuta and Naoto Chatani, Chem. Commun., 2012, Advance Article
Palladium-catalyzed aerobic oxidative C–H amination: synthesis of 2-unsubstituted and 2-substituted N-aryl benzimidazoles, Rapolu Kiran Kumar and Tharmalingam Punniyamurthy, RSC Adv., 2012, 2, 4616-4619
Single-electron oxidation of N-heterocyclic carbene-supported nickel amides yielding benzylic C–H activation, C. A. Laskowski, G. R. Morello, C. T. Saouma, T. R. Cundari and G. L. Hillhouse, Chem. Sci., 2012, Advance Article
Asymmetric catalytic carbon–carbon coupling reactions via C–H bond activation, Lei Yang and Hanmin Huang, Catal. Sci. Technol., 2012, 2, 1099-1112
C–C, C–O and C–N bond formation via rhodium(III)-catalyzed oxidative C–H activation, Guoyong Song, Fen Wang and Xingwei Li, Chem. Soc. Rev., 2012, 41, 3651-3678
Intramolecular catalytic asymmetric carbon–hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches, Michael P. Doyle, Maxim Ratnikov and Yu Liu, Org. Biomol. Chem., 2011, 9, 4007-4016
Dehydrogenative coupling reactions catalysed by Rose Bengal using visible light irradiation, Yuanhang Pan, Choon Wee Kee, Li Chen and Choon-Hong Tan, Green Chem., 2011, 13, 2682-2685
An efficient labeling strategy of drug like molecules with functionalized alkyl linkers using CH-activation, Jana Rentner and Rolf Breinbauer, Chem. Commun., 2012, 48, 10343-10345
C(naphthyl)–H bond activation by rhodium: isolation, characterization and TD-DFT study of the cyclometallates, Achintesh Narayan Biswas, Purak Das, Sandip Sengupta, Amitava Choudhury and Pinaki Bandyopadhyay, RSC Adv., 2011, 1, 1279-1286
An improved catalyst architecture for rhodium(III) catalyzed C–H activation and its application to pyridone synthesis, Todd K. Hyster and Tomislav Rovis, Chem. Sci., 2011, 2, 1606-1610
Direct C–H bond arylations and alkenylations with phenol-derived fluorine-free electrophiles, Sergei I. Kozhushkov, Harish Kumar Potukuchi and Lutz Ackermann, Catal. Sci. Technol., 2013, Advance Article
Towards mild metal-catalyzed C–H bond activation, Joanna Wencel-Delord, Thomas Dröge, Fan Liu and Frank Glorius, Chem. Soc. Rev., 2011, 40, 4740-4761
Palladium-catalyzed silyl C(sp3)–H bond activation, Yun Liang, Weizhi Geng, Junnian Wei, Kunbing Ouyang and Zhenfeng Xi, Org. Biomol. Chem., 2012, 10, 1537-1542
“On water”-promoted direct alkynylation of isatins catalyzed by NHC–silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones, Xiao-Pu Fu, Li Liu, Dong Wang, Yong-Jun Chen and Chao-Jun Li, Green Chem., 2011, 13, 549-553
Rare-earth metal complexes having an unusual indolyl-1,2-dianion through C–H activation with a novel η1(μ2–η1:η1) bonding with metals, Xiancui Zhu, Shuangliu Zhou, Shaowu Wang, Yun Wei, Lijun Zhang, Fenhua Wang, Shaoyin Wang and Zhijun Feng, Chem. Commun., 2012, Advance Article
Copper-catalysed addition of α-alkyl azaarenes to ethyl glyoxylate via direct C(sp3)–H activation, Jia-Jia Jin, Hong-Ying Niu, Gui-Rong Qu, Hai-Ming Guo and John S. Fossey, RSC Adv., 2012, 2, 5968-5971
Copper-catalyzed decarboxylative alkenylation of sp3 C–H bonds with cinnamic acids via a radical process, Zili Cui, Xiaojie Shang, Xiang-Feng Shao and Zhong-Quan Liu, Chem. Sci., 2012, 3, 2853-2858
Challenge and progress: palladium-catalyzed sp3 C–H activation, Hu Li, Bi-Jie Li and Zhang-Jie Shi, Catal. Sci. Technol., 2011, 1, 191-206
Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formation, Seung Hwan Cho, Ji Young Kim, Jaesung Kwak and Sukbok Chang, Chem. Soc. Rev., 2011, 40, 5068-5083
Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation, B. V. Subba Reddy, Prashant Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and René Grée, Org. Biomol. Chem., 2012, 10, 1349-1358
An efficient copper-catalyzed formation of highly substituted pyrazoles using molecular oxygen as the oxidant, Mamta Suri, Thierry Jousseaume, Julia J. Neumann and Frank Glorius, Green Chem., 2012, 14, 2193-2196
Synthesis of fused N-heterocycles via tandem C–H activation, Ge Meng, Hong-Ying Niu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li and Hai-Ming Guo, Chem. Commun., 2012, 48, 9601-9603
Activation of aliphatic C–H bonds by tetracyanobenzene photosensitization. A time-resolved and steady-state investigation, Stefano Protti, Maurizio Fagnoni, Sandra Monti, Julien Réhault, Olivier Poizat and Angelo Albini, RSC Adv., 2012, 2, 1897-1904
Electrophilic aryl C–H amination by dimetal nitrides: correlating electronic structure with reactivity, George H. Timmer and John F. Berry, Chem. Sci., 2012, 3, 3038-3052
A reusable Mn(II)-dampy-MCM-41 system for single step amination of benzene to aniline using hydroxylamine, Sudarshan Singha and K. M. Parida, Catal. Sci. Technol., 2011, 1, 1496-1505
Diastereotopos-differentiating C–H activation reactions at methylene groups, Pavel Herrmann and Thorsten Bach, Chem. Soc. Rev., 2011, 40, 2022-2038
Gold-mediated bifunctional modification of oligosaccharides via a three-component coupling reaction, Karen Ka-Yan Kung, Gai-Li Li, Lan Zou, Hiu-Chi Chong, Yun-Chung Leung, Ka-Hing Wong, Vanessa Kar-Yan Lo, Chi-Ming Che and Man-Kin Wong, Org. Biomol. Chem., 2012, 10, 925-930
The direct carboxylation of terminal alkynes with carbon dioxide, Yu Dingyi and Zhang Yugen, Green Chem., 2011, 13, 1275-1279
Pd-catalyzed double C–H bond activation of diaryl ketones for the synthesis of fluorenones, Parthasarathy Gandeepan, Chen-Hsun Hung and Chien-Hong Cheng, Chem. Commun., 2012, 48, 9379-9381
One-pot solvent-free synthesis of quinolines by C–H activation/C–C Bond formation catalyzed by recyclable iron(III) triflate, Changsheng Yao, Bingbin Qin, Honghong Zhang, Jun Lu, Donglin Wang and Shujiang Tu, RSC Adv., 2012, 2, 3759-3764
Direct Sp3 α-C–H activation and functionalization of alcohol and ether, Shu-Yu Zhang, Fu-Min Zhang and Yong-Qiang Tu, Chem. Soc. Rev., 2011, 40, 1937-1949
Asymmetric catalytic carbon–carbon coupling reactions via C–H bond activation, Lei Yang and Hanmin Huang, Catal. Sci. Technol., 2012, 2, 1099-1112
Room temperature reversible C–H activation mediated by a Pt(0) center, and stoichiometric biphenyl formation via solvent activation, Emmanuel Nicolas, Xavier-Frédéric le Goff, Stéphane Bouchonnet and Nicolas Mézailles, Chem. Commun., 2012, 48, 8350-8352
For even more articles take a look at the Chem. Soc. Rev Themed Issue C–H Functionalisation in organic synthesis.
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