Copper-catalyzed tandem oxidation-olefination process.
作者： Michaël Davi , Hélène Lebel
DOI: 10.1021/OL802299D
关键词: Catalysis 、 Chemistry 、 Combinatorial chemistry 、 Copper 、 Large range 、 Tandem 、 Reaction conditions 、 Nanotechnology 、 Racemization 、 Copper catalyzed
摘要: A novel catalytic sequence aerobic oxidation−olefination has been developed. single and inexpensive copper catalyst provides a large range of olefins from alcohols in good to excellent yields. The reaction exhibits functional group compatibility, the nonbasic conditions allow transformation chiral substrates without racemization.
acs.org
sci-hub.se 参考文章(70)
Hongxing Zhang, Maddi Sridhar Reddy, Serge Phoenix, Pierre Deslongchamps, Total Synthesis of Ouabagenin and Ouabain Angewandte Chemie. ,vol. 47, pp. 1272- 1275 ,(2008) , 10.1002/ANIE.200704959
David R. Jensen, Mitchell J. Schultz, Jaime A. Mueller, Matthew S. Sigman, A Well-Defined Complex for Palladium-Catalyzed Aerobic Oxidation of Alcohols: Design, Synthesis, and Mechanistic Considerations Angewandte Chemie International Edition. ,vol. 42, pp. 3810- 3813 ,(2003) , 10.1002/ANIE.200351997
Hélène Lebel, Valérie Paquet, Caroline Proulx, Methylenation of Aldehydes: Transition Metal Catalyzed Formation of Salt-Free Phosphorus Ylides Angewandte Chemie International Edition. ,vol. 40, pp. 2887- 2890 ,(2001) , 10.1002/1521-3773(20010803)40:15<2887::AID-ANIE2887>3.0.CO;2-Q
Matthew S. Sigman, David R. Jensen, Ligand-Modulated Palladium-Catalyzed Aerobic Alcohol Oxidations Accounts of Chemical Research. ,vol. 39, pp. 221- 229 ,(2006) , 10.1021/AR040243M
Jangari Santhosh Reddy, Batchu Venkateswara Rao, A Short, Efficient, and Stereoselective Total Synthesis of a Pyrrolidine Alkaloid: (−)-Codonopsinine† Journal of Organic Chemistry. ,vol. 72, pp. 2224- 2227 ,(2007) , 10.1021/JO061940Q
Hélène Lebel, Michaël Davi, Silvia Díez-González, Steven P. Nolan, Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes. Journal of Organic Chemistry. ,vol. 72, pp. 144- 149 ,(2007) , 10.1021/JO061781A
Hideo Nagashima, Mitsuru Gondo, Satoshi Masuda, Hideo Kondo, Yoshitaka Yamaguchi, Kouki Matsubara, Organoruthenium(II) and (III) amidinates, (η5-C5Me5)Ru(η-amidinate) and (η5-C5Me5)RuCl(η-amidinate), as unique redox catalysts for the intramolecular Kharasch reactions: Facile access to a pyrrolizidine alkaloid skeleton under mild conditions Chemical Communications. ,vol. 3, pp. 442- 443 ,(2003) , 10.1039/B209369C
Fernando R. Pinacho Crisóstomo, Romen Carrillo, Tomás Martín, Fernando García-Tellado, Víctor S. Martín, A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols. Journal of Organic Chemistry. ,vol. 70, pp. 10099- 10101 ,(2005) , 10.1021/JO051566E
Mitchell J. Schultz, Steven S. Hamilton, David R. Jensen, Matthew S. Sigman, Development and comparison of the substrate scope of Pd-catalysts for the aerobic oxidation of alcohols. Journal of Organic Chemistry. ,vol. 70, pp. 3343- 3352 ,(2005) , 10.1021/JO0482211
IstvN. E. Mark, Paul R. Giles, Masao Tsukazaki, Arnaud Gautier, Raphal Dumeunier, Kanae Doda, Freddi Philippart, Isabelle Chell-Regnault, Jean-Luc Mutonkole, Stephen M. Brown, Christopher J. Urch, Chapter 2.13. Aerobic, Metal-Catalyzed Oxidation of Alcohols Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, Second Revised and Enlarged Edition. ,(2008) , 10.1002/9783527619405.CH5M