Copper-Catalyzed Oxidative Coupling of Alkenes with Aldehydes: Direct Access to α,β-Unsaturated Ketones†
Jing Wang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
These authors contributed equally to this work.
Search for more papers by this authorDr. Chao Liu
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
These authors contributed equally to this work.
Search for more papers by this authorJiwen Yuan
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
Search for more papers by this authorCorresponding Author
Prof. Aiwen Lei
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, 430071 (P. R. China)
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/===Search for more papers by this authorJing Wang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
These authors contributed equally to this work.
Search for more papers by this authorDr. Chao Liu
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
These authors contributed equally to this work.
Search for more papers by this authorJiwen Yuan
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
Search for more papers by this authorCorresponding Author
Prof. Aiwen Lei
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, 430071 (P. R. China)
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei (P. R. China) http://www.chem.whu.edu.cn/GCI_WebSite/===Search for more papers by this authorThis work was supported by the 973 Program (2012CB725302), the National Natural Science Foundation of China (21025206 and 21272180), and the China Postdoctoral Science Foundation funded project (2012M521458). We are also grateful for the support from the Program for Changjiang Scholars and Innovative Research Team in University (IRT1030).
Graphical Abstract
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange_201208920_sm_miscellaneous_information.pdf1.8 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aC. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633–639;
- 1bT. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, Org. Lett. 2007, 9, 3137–3139;
- 1cS. Potavathri, A. S. Dumas, T. Dwight, G. R. Naumiec, J. M. Hammann, B. Deboef, Tetrahedron Lett. 2008, 49, 4050–4053;
- 1dC.-j. Li, Acc. Chem. Res. 2009, 42, 335–344;
- 1eG. P. Mcglacken, L. M. Bateman, L. Bateman, Chem. Soc. Rev. 2009, 38, 2447–2464;
- 1fD. Shabashov, Acc. Chem. Res. 2009, 42, 1074–1086;
- 1gJ. A. Ashenhurst, Chem. Soc. Rev. 2010, 39, 540–548;
- 1hS. Potavathri, K. C. Pereira, S. I. Gorelsky, A. Pike, A. P. LeBris, B. DeBoef, J. Am. Chem. Soc. 2010, 132, 14676–14681;
- 1iS. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068–5083;
- 1jA. Kantak, S. Potavathri, R. Barham, K. M. Romano, B. DeBoef, J. Am. Chem. Soc. 2011, 133, 19960–19965;
- 1kJ. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170–1214;
- 1lC. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780–1824;
- 1mS. Potavathri, A. Kantak, B. DeBoef, Chem. Commun. 2011, 47, 4679–4681.
- 2
- 2aC.-W. Chan, Z. Zhou, A. S. C. Chan, W.-Y. Yu, Org. Lett. 2010, 12, 17;
- 2bX. Jia, S. Zhang, W. Wang, F. Luo, J. Cheng, Org. Lett. 2009, 11, 3120–3123;
- 2cM. Al-Masum, E. Ng, M. C. Wai, Tetrahedron Lett. 2011, 52, 1008–1010;
- 2dB.-X. Tang, R.-J. Song, J.-H. Li, J. Am. Chem. Soc. 2010, 132, 8900–8902;
- 2eY. Wu, B. Li, F. Mao, X. Li, F. Y. Kwong, Org. Lett. 2011, 13, 3261–3264.
- 3
- 3aW. Wu, H. Jiang, Acc. Chem. Res. 2012, 45, 1736–1748;
- 3bC. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215–1292.
- 4Z. Shi, N. Schröder, F. Glorius, Angew. Chem. 2012, 124, 8216–8220; Angew. Chem. Int. Ed. 2012, 51, 8092–8096.
- 5
- 5aV. Chudasama, R. J. Fitzmaurice, S. Caddick, Nat. Chem. 2010, 2, 592–596;
- 5bS. Tsujimoto, T. Iwahama, S. Sakaguchi, Y. Ishii, Chem. Commun. 2001, 2352–2353;
- 5cS. Tsujimoto, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 2003, 44, 5601–5604.
- 6W. Liu, Y. Li, K. Liu, Z. Li, J. Am. Chem. Soc. 2011, 133, 10756–10759.
- 7N. K. Sahu, S. S. Balbhadra, J. Choudhary, D. V. Kohli, Curr. Med. Chem. 2012, 19, 209–225.
- 8
- 8aK. Y. Koltunov, S. Walspurger, J. Sommer, Tetrahedron Lett. 2005, 46, 8391–8394;
- 8bY. Liang, D. Dong, Y. Lu, Y. Wang, W. Pan, Y. Chai, Q. Liu, Synthesis 2006, 3301–3304;
- 8cA. Saito, M. Umakoshi, N. Yagyu, Y. Hanzawa, Org. Lett. 2008, 10, 1783–1785;
- 8dK. Murugan, S. Srimurugan, C. Chen, Chem. Commun. 2010, 46, 1127–1129;
- 8eJ. Wang, X. Wang, Z. Ge, T. Cheng, R. Li, Chem. Commun. 2010, 46, 1751–1753;
- 8fY.-K. Liu, J. Zhu, J.-Q. Qian, B. Jiang, Z.-Y. Xu, J. Org. Chem. 2011, 76, 9096–9101;
- 8gS. Ma, L. Wu, M. Liu, Y. Wang, Org. Biomol. Chem. 2012, 10, 3721–3729;
- 8hO. Mahé, I. Dez, V. Levacher, J.-F. Brière, Org. Biomol. Chem. 2012, 10, 3946–3954.
- 9
- 9aK. Yoshizawa, T. Shioiri, Tetrahedron Lett. 2006, 47, 4943–4945;
- 9bJ. S. Yadav, B. V. Subba Reddy, P. Vishnumurthy, Tetrahedron Lett. 2008, 49, 4498–4500;
- 9cS. Kim, S. W. Bae, J. S. Lee, J. Park, Tetrahedron 2009, 65, 1461–1466;
- 9dM. Egi, M. Umemura, T. Kawai, S. Akai, Angew. Chem. 2011, 123, 12405–12408;
10.1002/ange.201106381 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 12197–12200;
- 9eF. Fang, Y. Li, S.-K. Tian, Eur. J. Org. Chem. 2011, 1084–1091;
- 9fM. N. Pennell, M. G. Unthank, P. Turner, T. D. Sheppard, J. Org. Chem. 2011, 76, 1479–1482;
- 9gA. Antiñolo, F. Carrillo-Hermosilla, V. Cadierno, J. Garcia-Alvarez, A. Otero, ChemCatChem 2012, 4, 123–128;
- 9hS. Liao, K. Yu, Q. Li, H. Tian, Z. Zhang, X. Yu, Q. Xu, Org. Biomol. Chem. 2012, 10, 2973–2978;
- 9iJ. Schranck, X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 4827–4831;
- 9jX.-F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 282–285.
- 10C. Liu, S. Tang, D. Liu, J. Yuan, L. Zheng, L. Meng, A. Lei, Angew. Chem. 2012, 124, 3698–3701; Angew. Chem. Int. Ed. 2012, 51, 3638–3641.
- 11
- 11aC. Chatgilialoglu, D. Crich, M. Komatsu, I. Ryu, Chem. Rev. 1999, 99, 1991;
- 11bC. Li, L. Wang, P. Li, W. Zhou, Chem. Eur. J. 2011, 17, 10208–10212.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.