Ligand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions
作者： Sarah E. Walker , Julian Boehnke , Pauline E. Glen , Steven Levey , Lisa Patrick
DOI: 10.1021/OL400539H
关键词:
摘要: A simple change of solvent allows controlled and efficient switching between oxidative Heck conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both are ligand- base-free tolerant air moisture, the sheds light some factors which favor one reaction over other.
acs.org
hw.ac.uk
strath.ac.uk
sci-hub.se 参考文章(51)
Takashi Nishikata, Yasunori Yamamoto, Norio Miyaura, Conjugate Addition of Aryl Boronic Acids to Enones Catalyzed by Cationic Palladium(II)–Phosphane Complexes Angewandte Chemie International Edition. ,vol. 42, pp. 2768- 2770 ,(2003) , 10.1002/ANIE.200350888
Laura A. Brozek, Joshua D. Sieber, James P. Morken, Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones. Organic Letters. ,vol. 13, pp. 995- 997 ,(2011) , 10.1021/OL102982B
Daisuke Tanaka, Andrew G. Myers, Heck-Type Arylation of 2-Cycloalken-1-ones with Arylpalladium Intermediates Formed by Decarboxylative Palladation and by Aryl Iodide Insertion Organic Letters. ,vol. 6, pp. 433- 436 ,(2004) , 10.1021/OL0363467
Andrey Gutnov, Palladium-Catalyzed Asymmetric Conjugate Addition of Aryl-Metal Species European Journal of Organic Chemistry. ,vol. 2008, pp. 4547- 4554 ,(2008) , 10.1002/EJOC.200800541
Tianning Diao, Shannon S. Stahl, Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones. Journal of the American Chemical Society. ,vol. 133, pp. 14566- 14569 ,(2011) , 10.1021/JA206575J
Yacoub Fall, Henri Doucet, Maurice Santelli, Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one Tetrahedron. ,vol. 65, pp. 489- 495 ,(2009) , 10.1016/J.TET.2008.11.006
Kotaro Kikushima, Jeffrey C. Holder, Michele Gatti, Brian M. Stoltz, Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters. Journal of the American Chemical Society. ,vol. 133, pp. 6902- 6905 ,(2011) , 10.1021/JA200664X
Shaohui Lin, Xiyan Lu, Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers Organic Letters. ,vol. 12, pp. 2536- 2539 ,(2010) , 10.1021/OL100767U
James D. Crowley, Kevin D. Hänni, Ai-Lan Lee, David A. Leigh, [2]Rotaxanes through palladium active-template oxidative heck cross-couplings. Journal of the American Chemical Society. ,vol. 129, pp. 12092- 12093 ,(2007) , 10.1021/JA075219T
Peng Sun, Yan Zhu, Hailong Yang, Hong Yan, Linhua Lu, Xiang Zhang, Jincheng Mao, The ligand and base-free Pd-catalyzed oxidative Heck reaction of arylboronic acids and olefins. Organic and Biomolecular Chemistry. ,vol. 10, pp. 4512- 4515 ,(2012) , 10.1039/C2OB25462J