Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex

作者: Ramesh Giri , Nathan Maugel , Bruce M. Foxman , Jin-Quan Yu

DOI: 10.1021/OM8000444

关键词:

摘要: Pd(OAc)2-mediated dehydrogenation of an alkyl group to a double bond or η3-allylic complex via sp3 C−H activation and allylic oxidation is reported. A novel redox proposed for this under oxidant-free conditions. catalytic protocol using benzoquinone as the stoichiometric oxidant has also been developed cyclopentylcarboxamides.

参考文章(74)
Dipannita Kalyani, Melanie S. Sanford, Regioselectivity in palladium-catalyzed C-H activation/oxygenation reactions. Organic Letters. ,vol. 7, pp. 4149- 4152 ,(2005) , 10.1021/OL051486X
Ramesh Giri, Xiao Chen, Xue-Shi Hao, Jiao-Jie Li, Jue Liang, Zi-Peng Fan, Jin-Quan Yu, Catalytic and stereoselective iodination of prochiral C-H bonds Tetrahedron-asymmetry. ,vol. 16, pp. 3502- 3505 ,(2005) , 10.1016/J.TETASY.2005.08.049
Shangdong Yang, Bijie Li, Xiaobing Wan, Zhangjie Shi, Ortho Arylation of Acetanilides via Pd(II)-Catalyzed C−H Functionalization Journal of the American Chemical Society. ,vol. 129, pp. 6066- 6067 ,(2007) , 10.1021/JA070767S
Takeo Izumi, Hiroyuki Watabe, Akira Kasahara, The σ-Bonded Palladium(II) Complexes of 2-Aryl-4,4-dimethyl-2-oxazolines Bulletin of the Chemical Society of Japan. ,vol. 54, pp. 1711- 1714 ,(1981) , 10.1246/BCSJ.54.1711
Alexander D. Ryabov, Cyclopalladated complexes in organic synthesis Synthesis. ,vol. 1985, pp. 233- 252 ,(1985) , 10.1055/S-1985-31169
Ramesh Giri, Masayuki Wasa, Steven P. Breazzano, Jin-Quan Yu, Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization. Organic Letters. ,vol. 8, pp. 5685- 5688 ,(2006) , 10.1021/OL0618858
Ramesh Giri, Nathan Maugel, Jiao-Jie Li, Dong-Hui Wang, Steven P. Breazzano, Lindsey B. Saunders, Jin-Quan Yu, Palladium-Catalyzed Methylation and Arylation of sp2 and sp3 C−H Bonds in Simple Carboxylic Acids Journal of the American Chemical Society. ,vol. 129, pp. 3510- 3511 ,(2007) , 10.1021/JA0701614
Kami L. Hull, Erica L. Lanni, Melanie S. Sanford, Highly Regioselective Catalytic Oxidative Coupling Reactions: Synthetic and Mechanistic Investigations Journal of the American Chemical Society. ,vol. 128, pp. 14047- 14049 ,(2006) , 10.1021/JA065718E
Dmitry Shabashov, Olafs Daugulis, ortho-Arylation of Benzamides Organic Letters. ,vol. 8, pp. 4947- 4949 ,(2006) , 10.1021/OL0619866
Mukta Gupta, Chrystel Hagen, William C. Kaska, Roger E. Cramer, Craig M. Jensen, Catalytic Dehydrogenation of Cycloalkanes to Arenes by a Dihydrido Iridium P−C−P Pincer Complex Journal of the American Chemical Society. ,vol. 119, pp. 840- 841 ,(1997) , 10.1021/JA962560X