Transition‐Metal‐Catalyzed Carbonylative Domino Reactions

作者: Xiao-Feng Wu , Helfried Neumann , Matthias Beller

DOI: 10.1002/9783527671304.CH1

关键词:

摘要: ‘‘Sustainable development’’ has become one of the hottest terms in twenty-first century. Of particular relevance organic chemistry are reaction efficiency and avoidance waste generation. With regard to sustainability, methodologies based on domino reactions, including multicomponent a highly efficient strategy synthesize complicated compounds. Domino reactions defined as processes two or more bond-forming under identical conditions, which subsequent transformations take place at functionalities that obtained previous transformations. Using compounds can be relatively easily prepared from simple substrates. No tedious preparation intermediates purification needed, most energy-consuming waste-generating steps synthesis [1]. One prominent example is Knoevenagel/hetero-Diels–Alder reaction, dihydropyrans could straightforwardly synthesized readily available starting materials [2]. Transition-metal catalysts play an ever-increasing important role modern [3]. Numerous transition-metal-catalyzed coupling have been developed applied total natural products, such Suzuki theNegishi theHeck andmany others [4]. Interestingly, power transition-metal even visible area where palladium walking show value transition metals bond formations. Carbonylation interesting with both industrial academic research [5]. In these carbonmonoxide (CO) used cheapest C1 sources. By introducing CO units into parent molecules, carbonyl-containing products prepared, further modified yield chemicals for synthesis. Following definition we realized our surprise all carbonylative belong least C–C bonds were formed same conditions.

参考文章(126)
Ranjan Jana, Tejas P. Pathak, Matthew S. Sigman, Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chemical Reviews. ,vol. 111, pp. 1417- 1492 ,(2011) , 10.1021/CR100327P
Jianming Liu, Rongzhao Zhang, Shoufeng Wang, Wei Sun, Chungu Xia, A general and efficient copper catalyst for the double carbonylation reaction. Organic Letters. ,vol. 11, pp. 1321- 1324 ,(2009) , 10.1021/OL9001027
Chan Sik Cho, Hyung Sup Shim, Heung-Jin Choi, Tae-Jeong Kim, Sang Chul Shim, Myung Chul Kim, Synthesis of isoindolin-1-ones via palladium-catalyzed intermolecular coupling and heteroannulation between 2-iodobenzoyl chloride and imines Tetrahedron Letters. ,vol. 41, pp. 3891- 3893 ,(2000) , 10.1016/S0040-4039(00)00495-0
Adam F. Littke, Gregory C. Fu, Palladium-Catalyzed Coupling Reactions of Aryl Chlorides Angewandte Chemie International Edition. ,vol. 41, pp. 4176- 4211 ,(2002) , 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Lutz F Tietze, Monika E Lieb, Domino reactions for library synthesis of small molecules in combinatorial chemistry. Current Opinion in Chemical Biology. ,vol. 2, pp. 363- 371 ,(1998) , 10.1016/S1367-5931(98)80010-0
Marta Rosillo, Eduardo Arnáiz, Delbrin Abdi, Jaime Blanco-Urgoiti, Gema Domínguez, Javier Pérez-Castells, Combination of RCM and the Pauson–Khand Reaction: One‐Step Synthesis of Tricyclic Structures European Journal of Organic Chemistry. ,vol. 2008, pp. 3917- 3927 ,(2008) , 10.1002/EJOC.200800332
Xiao-Feng Wu, Basker Sundararaju, Pazhamalai Anbarasan, Helfried Neumann, Pierre H. Dixneuf, Matthias Beller, A general cyclocarbonylation of aryl bromides and triflates with acetylenes: palladium-catalyzed synthesis of 3-alkylidenefuran-2-ones. Chemistry: A European Journal. ,vol. 17, pp. 8014- 8017 ,(2011) , 10.1002/CHEM.201101083
Mariappan Periasamy, Ukkiramapandian Radhakrishnan, Jean-Jacques Brunet, Remi Chauvin, Abdel Wahed El Zaizi, Double carbonylation of alkynes using NaHFe(CO)4 Chemical Communications. pp. 1499- 1500 ,(1996) , 10.1039/CC9960001499
Yoshio Inoue, Kunihiro Ohuchi, I-Fang Yen, Shin Imaizumi, Preparation of 3(2H)-Furanones from 2-Propynyl Alcohol, CO, and Phenyl Halides under CO2Atmosphere Catalyzed by Transition Metal Complexes Bulletin of the Chemical Society of Japan. ,vol. 62, pp. 3518- 3522 ,(1989) , 10.1246/BCSJ.62.3518