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Pure Appl. Chem., 2006, Vol. 78, No. 5, pp. 935-945

http://dx.doi.org/10.1351/pac200678050935

Green chemistry: The development of cross-dehydrogenative coupling (CDC) for chemical synthesis

Chao-Jun Li and Zhiping Li

Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, H3A 2K6, Canada

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  • Girard Simon A., Knauber Thomas, Li Chao-Jun: Dehydrierende Kreuzkupplungen von C sp 3-H-Bindungen: vielseitige Verfahren zur Bildung von C-C-Bindungen. Angew. Chem. 2014, 126, 76. <http://dx.doi.org/10.1002/ange.201304268>
  • Girard Simon A., Knauber Thomas, Li Chao-Jun: The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations. Angew. Chem. Int. Ed. 2014, 53, 74. <http://dx.doi.org/10.1002/anie.201304268>
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  • Li Yuanming, Jia Fan, Li Zhiping: Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Aldehydes. Chem. Eur. J. 2013, 19, 82. <http://dx.doi.org/10.1002/chem.201203824>
  • Fu Xiao-Pu, Xuan Qing-Qing, Liu Li, Wang Dong, Chen Yong-Jun, Li Chao-Jun: Dual C–H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides. Tetrahedron 2013, 69, 4436. <http://dx.doi.org/10.1016/j.tet.2012.10.048>
  • Huang Xing-Fen, Zhu Zhi-Qiang, Huang Zhi-Zhen: Copper-catalyzed dehydrogenative cross-coupling reaction between unactivated ethers and simple ketones mediated by pyrrolidine. Tetrahedron 2013, 69, 8579. <http://dx.doi.org/10.1016/j.tet.2013.07.085>
  • Wang Gao, Yu Qing-Ying, Chen Shan-Yong, Yu Xiao-Qi: Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates. Tetrahedron Letters 2013. <http://dx.doi.org/10.1016/j.tetlet.2013.09.006>
  • Suess Alison M., Ertem Mehmed Z., Cramer Christopher J., Stahl Shannon S.: Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C–H Oxidation. J. Am. Chem. Soc. 2013, 135, 9797. <http://dx.doi.org/10.1021/ja4026424>
  • Li Yuanming, Ma Lina, Jia Fan, Li Zhiping: Amide Bond Formation through Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Anhydrides. J. Org. Chem. 2013, 78, 5638. <http://dx.doi.org/10.1021/jo400804p>
  • Zhou Shengbin, Wang Jiang, Lin Daizong, Zhao Fei, Liu Hong: Enantioselective Synthesis of 2-Substitued-Tetrahydroisoquinolin-1-yl Glycine Derivatives via Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines and Chiral Nickel(II) Glycinate. J. Org. Chem. 2013, 78, 11204. <http://dx.doi.org/10.1021/jo401510b>
  • Nie Shao-zhen, Sun Xiang, Wei Wen-tao, Zhang Xue-jing, Yan Ming, Xiao Jian-liang: Unprecedented Construction of C═C Double Bonds via Ir-Catalyzed Dehydrogenative and Dehydrative Cross-Couplings. Org. Lett. 2013, 15, 2394. <http://dx.doi.org/10.1021/ol4008469>
  • Yang Bin, Yang Ting-Ting, Li Xi-An, Wang Jun-Jiao, Yang Shang-Dong: A Mild, Selective Copper-Catalyzed Oxidative Phosphonation of α-Amino Ketones. Org. Lett. 2013, 15, 5024. <http://dx.doi.org/10.1021/ol402355a>
  • Zhang Shuai, Guo Li-Na, Wang Hua, Duan Xin-Hua: Bu4NI-catalyzed decarboxylative acyloxylation of an sp3 C–H bond adjacent to a heteroatom with α-oxocarboxylic acids. Org. Biomol. Chem. 2013, 11, 4308. <http://dx.doi.org/10.1039/c3ob40748a>
  • Chen Li, Chao Chin Sheng, Pan Yuanhang, Dong Sheng, Teo Yew Chin, Wang Jian, Tan Choon-Hong: Amphiphilic methyleneamino synthon through organic dye catalyzed-decarboxylative aminoalkylation. Org. Biomol. Chem. 2013, 11, 5922. <http://dx.doi.org/10.1039/c3ob41091a>
  • Chen Jianbin, Liu Bin, Liu Dongfang, Liu Shan, Cheng Jiang: The Copper-Catalyzed C-3-Formylation of Indole CH Bonds using Tertiary Amines and Molecular Oxygen. Adv. Synth. Catal. 2012, 354, 2438. <http://dx.doi.org/10.1002/adsc.201200345>
  • Tian Haiwen, Yu Xiaochun, Li Qiang, Wang Jianxin, Xu Qing: General, Green, and Scalable Synthesis of Imines from Alcohols and Amines by a Mild and Efficient Copper-Catalyzed Aerobic Oxidative Reaction in Open Air at Room Temperature. Adv. Synth. Catal. 2012, 354, 2671. <http://dx.doi.org/10.1002/adsc.201200574>
  • Lin Li, Zhang Jinlong, Wang Rui: One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Alkynes and Activated Nitroalkanes. Asian Journal of Organic Chemistry 2012, 1, 222. <http://dx.doi.org/10.1002/ajoc.201200058>
  • Xie Jin, Li Huamin, Zhou Jiecong, Cheng Yixiang, Zhu Chengjian: A Highly Efficient Gold-Catalyzed Oxidative CC Coupling from CH Bonds Using Air as Oxidant. angew chemie 2012, 124, 1278. <http://dx.doi.org/10.1002/ange.201107605>
  • Yamaguchi Junichiro, Yamaguchi Atsushi D., Itami Kenichiro: Funktionalisierung von C-H-Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika. Angew. Chem. 2012, 124, 9092. <http://dx.doi.org/10.1002/ange.201201666>
  • Wang Teng, Zhou Wang, Yin Hang, Ma Jun-An, Jiao Ning: Iron-Facilitated Oxidative Dehydrogenative CO Bond Formation by Propargylic C sp 3H Functionalization. Angew. Chem. 2012, 124, 10981. <http://dx.doi.org/10.1002/ange.201205779>
  • Xu Zejun, Zhang Chun, Jiao Ning: Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines. Angew. Chem. 2012, 124, 11529. <http://dx.doi.org/10.1002/ange.201206382>
  • Xie Jin, Li Huamin, Zhou Jiecong, Cheng Yixiang, Zhu Chengjian: A Highly Efficient Gold-Catalyzed Oxidative CC Coupling from CH Bonds Using Air as Oxidant. Angew Chem Int E 2012, 51, 1252. <http://dx.doi.org/10.1002/anie.201107605>
  • Yamaguchi Junichiro, Yamaguchi Atsushi D., Itami Kenichiro: CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals. Angew. Chem. Int. Ed. 2012, 51, 8960. <http://dx.doi.org/10.1002/anie.201201666>
  • Wang Teng, Zhou Wang, Yin Hang, Ma Jun-An, Jiao Ning: Iron-Facilitated Oxidative Dehydrogenative CO Bond Formation by Propargylic C sp 3H Functionalization. Angew. Chem. Int. Ed. 2012, 51, 10823. <http://dx.doi.org/10.1002/anie.201205779>
  • Xu Zejun, Zhang Chun, Jiao Ning: Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines. Angew. Chem. Int. Ed. 2012, 51, 11367. <http://dx.doi.org/10.1002/anie.201206382>
  • Mitchell Emily A., Peschiulli Aldo, Lefevre Nicolas, Meerpoel Lieven, Maes Bert U. W.: Direct α-Functionalization of Saturated Cyclic Amines. Chem. Eur. J. 2012, 18, 10092. <http://dx.doi.org/10.1002/chem.201201539>
  • Li Jiangsheng, Cai Feifei, Li Zhiwei, Xue Yuan, Cheng Chao, Liu Weidong, Cao Zhong: Domino Cross Dehydrogenative Coupling of 2-Aryl Acetals with Ketones Using DDQ as Oxidant and Reactant Precursor. Chin. J. Chem. 2012, 30, 1699. <http://dx.doi.org/10.1002/cjoc.201200302>
  • Fu Weijun, Guo Wenbo, Zou Guanglong, Xu Chen: Selective trifluoromethylation and alkynylation of tetrahydroisoquinolines using visible light irradiation by Rose Bengal. Journal of Fluorine Chemistry 2012, 140, 88. <http://dx.doi.org/10.1016/j.jfluchem.2012.05.009>
  • Ghosh Santanu, De Subhadip, Kakde Badrinath N., Bhunia Subhajit, Adhikary Amit, Bisai Alakesh: Intramolecular Dehydrogenative Coupling of sp2 C–H and sp3 C–H Bonds: An Expeditious Route to 2-Oxindoles. Org. Lett. 2012, 14, 5864. <http://dx.doi.org/10.1021/ol302767w>
  • Liao Shiheng, Yu Kangkang, Li Qiang, Tian Haiwen, Zhang Zhengping, Yu Xiaochun, Xu Qing: Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology. Biomol Chem 2012, 10, 2973. <http://dx.doi.org/10.1039/c1ob06739g>
  • Li Qiang, Fan Songjian, Sun Qing, Tian Haiwen, Yu Xiaochun, Xu Qing: Copper-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology. Biomol Chem 2012, 10, 2966. <http://dx.doi.org/10.1039/c1ob06743e>
  • Zhang Bo, Cui Yuxin, Jiao Ning: Metal-free TEMPO-catalyzed oxidative C–C bond formation from Csp3–H bonds using molecular oxygen as the oxidant. Chem Commn 2012, 48, 4498. <http://dx.doi.org/10.1039/c2cc30684k>
  • Shi Zhuangzhi, Zhang Chun, Tang Conghui, Jiao Ning: Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant. Chemical Society Review 2012, 41, 3381. <http://dx.doi.org/10.1039/c2cs15224j>
  • Jiang Honglai, Xie Jin, Lin Aijun, Cheng Yixiang, Zhu Chengjian: The Au(iii)-catalyzed coupling reactions between alcohols and N-heterocycles via C–H bond activation. RSC Adv. 2012, 2, 10496. <http://dx.doi.org/10.1039/c2ra22120a>
  • Wendlandt Alison E., Suess Alison M., Stahl Shannon S.: Kupferkatalysierte aerobe oxidative C-H-Funktionalisierungen: Trends und Erkenntnisse zum Mechanismus. angew chemie 2011, 123, 11256. <http://dx.doi.org/10.1002/ange.201103945>
  • Zhang Gen, Zhang Yaohu, Wang Rui: Catalytic Asymmetric Activation of a C sp 3H Bond Adjacent to a Nitrogen Atom: A Versatile Approach to Optically Active α-Alkyl α-Amino Acids and C1-Alkylated Tetrahydroisoquinoline Derivatives. angew chemie 2011, 123, 10613. <http://dx.doi.org/10.1002/ange.201105123>
  • Wendlandt Alison E., Suess Alison M., Stahl Shannon S.: Copper-Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights. Angew Chem Int E 2011, 50, 11062. <http://dx.doi.org/10.1002/anie.201103945>
  • Zhang Gen, Zhang Yaohu, Wang Rui: Catalytic Asymmetric Activation of a C sp 3H Bond Adjacent to a Nitrogen Atom: A Versatile Approach to Optically Active α-Alkyl α-Amino Acids and C1-Alkylated Tetrahydroisoquinoline Derivatives. Angew. Chem. Int. Ed. 2011, 50, 10429. <http://dx.doi.org/10.1002/anie.201105123>
  • Richter Heinrich, Rohlmann Renate, García Mancheño Olga: Catalyzed Selective Direct α- and γ-Alkylation of Aldehydes with Cyclic Benzyl Ethers by Using T+BF4− in the Presence of an Inexpensive Organic Acid or Anhydride. Chemistry A European Journal 2011, 17, 11622. <http://dx.doi.org/10.1002/chem.201101786>
  • Li Chao-Jun: Unorthodox chemistry for an unorthodox challenge: Exploration of new chemical reactivities for a sustainable future. Sci China Chem 2011, 54, 1815. <http://dx.doi.org/10.1007/s11426-011-4414-8>
  • Jin Zhuang, Xu Bo, Hammond Gerald B.: Copper mediated oxidation of amides to imides by Selectfluor. Tetrahetron Lett 2011, 52, 1956. <http://dx.doi.org/10.1016/j.tetlet.2011.02.059>
  • Xia Qinqin, Chen Wanzhi, Qiu Huayu: Direct C–N Coupling of Imidazoles and Benzylic Compounds via Iron-Catalyzed Oxidative Activation of C–H Bonds. J Org Chern 2011, 110822010122092. <http://dx.doi.org/10.1021/jo201253m>
  • Zhang Bo, Xiang Shi-Kai, Zhang Li−He, Cui Yuxin, Jiao Ning: Organocatalytic Asymmetric Intermolecular Dehydrogenative α-Alkylation of Aldehydes Using Molecular Oxygen as Oxidant. Org Lett 2011, 13, 5212. <http://dx.doi.org/10.1021/ol202090a>
  • Guo Xingwei, Li Zhiping, Liu Weiping, Liu Jinhua, Ogawa Daisuke, Nishihara Yasushi: Iron-Catalyzed Oxidation of Tertiary Amines: Synthesis of β-1,3-Dicarbonyl Aldehydes by Three-Component C–C Couplings. Org Lett 2011, 13, 6272. <http://dx.doi.org/10.1021/ol202749x>
  • Li Hu, Li Bi-Jie, Shi Zhang-Jie: Challenge and progress: palladium-catalyzed sp3 C–H activation. Catal Sci Technol 2011, 1, 191. <http://dx.doi.org/10.1039/c0cy00076k>
  • Han Wei, Mayer Peter, Ofial Armin R.: Iron-Catalyzed Oxidative Mono- and Bis-Phosphonation of N,N-Dialkylanilines. Adv Synth Catal 2010, 352, 1667. <http://dx.doi.org/10.1002/adsc.201000092>
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  • Scheuermann Caroline J.: Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction. Chem Asian J 2010, 5, 436. <http://dx.doi.org/10.1002/asia.200900487>
  • Correia Camille A., Li Chao-Jun: Catalytic alkylation of benzylic C–H bonds with 1,3-dicarbonyl compounds utilizing oxygen as terminal oxidant. Tetrahetron Lett 2010, 51, 1172. <http://dx.doi.org/10.1016/j.tetlet.2009.12.080>
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  • Yang Jianguo, Wang Zhijing, Pan Fuyou, Li Yongmin, Bao Weiliang: CuBr-catalyzed selective oxidation of N-azomethine: highly efficient synthesis of methine-bridged bis-indole compounds. Org Biomol Chem 2010, 8, 2975. <http://dx.doi.org/10.1039/c004213g>
  • Shu Xing-Zhong, Yang Yan-Fang, Xia Xiao-Feng, Ji Ke-Gong, Liu Xue-Yuan, Liang Yong-Min: Platinum-catalyzed cross-dehydrogenative coupling reaction in the absence of oxidant. Org Biomol Chem 2010, 8, 4077. <http://dx.doi.org/10.1039/c0ob00261e>
  • Guo Xiangyu, Deng Guojun, Li Chao-Jun: Ruthenium-Catalyzed Oxidative Homo-Coupling of 2-Arylpyridines. Adv Synth Catal 2009, 351, 2071. <http://dx.doi.org/10.1002/adsc.200900375>
  • Ohta Masaki, Quick Matthias P., Yamaguchi Junichiro, Wünsch Bernhard, Itami Kenichiro: Fe-Catalyzed Oxidative Coupling of Heteroarenes and Methylamines. Chem Asian J 2009, 4, 1416. <http://dx.doi.org/10.1002/asia.200900157>
  • Voutchkova Adelina M., Crabtree Robert H.: Iridium-catalyzed benzylic C–H activation and functionalization of alkyl arenes. Journal of Molecular Catalysis A 2009, 312, 1. <http://dx.doi.org/10.1016/j.molcata.2009.07.019>
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  • Zhang Yuhua, Li Chao-Jun: Highly Efficient Direct Alkylation of Activated Methylene by Cycloalkanes. Eur J Org Chem 2007, 2007, 4654. <http://dx.doi.org/10.1002/ejoc.200700686>