Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp2 C—H Bond Activation

doi:10.6023/A13020198

Acta Chimica Sinica ›› 2013, Vol. 71 ›› Issue (05): 717-721.DOI: 10.6023/A13020198 Previous Articles Next Articles

Article

钯催化下肟醚导向的sp² C—H键邻位酰氧化反应

蔡海婷, 李丹丹, 刘姿, 王官武

中国科学技术大学化学系合肥微尺度物质科学国家实验室合肥 230026

投稿日期:2013-02-19 发布日期:2013-03-21
通讯作者: 王官武,gwang@ustc.edu.cn; Tel.: 0551-63607864; Fax: 0551-63607864 E-mail:gwang@ustc.edu.cn
基金资助:
项目受国家自然科学基金(No. 91021004)和安徽省高校省级自然科学研究重大项目(No. KJ2010ZD05)资助.

Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp² C—H Bond Activation

Cai Haiting, Li Dandan, Liu Zi, Wang Guanwu

Department of Chemistry and Hefei National Laboratory for Physical Sciences at Microscale, University of Science and Technology of China, Hefei, Anhui 230026

Received:2013-02-19 Published:2013-03-21
Supported by:
Project supported by the National Natural Science Foundation of China (No. 91021004) and the Intercollegiate Key Project of Natural Sciences of Anhui Province, China (No. KJ2010ZD05).

1. Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp² C—H Bond Activation.PDF(4235KB)

Abstract

The palladium-catalyzed decarboxylative ortho-acylation of O-methyl ketoximes with α-oxocarboxylic acids in the presence of Na₂S₂O₈ and Ag₂O is demonstrated. This protocol can be applied to various O-methyl ketoximes and α-oxocarboxylic acids with both electron-donating and electron-withdrawing groups with products yields up to 98%.

Key words: palladium catalysis, C—H bond activation, O-methyl ketoximes-directed, decarboxylation, acylation

Cite this article

Cai Haiting, Li Dandan, Liu Zi, Wang Guanwu. Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp² C—H Bond Activation[J]. Acta Chimica Sinica, 2013, 71(05): 717-721.

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[1] (a) Hansen, M. R.; Hurley, L. H. Acc. Chem. Res. 1996, 29, 249;(b) Ma, D.; Jiang, Y.; Chen, F.; Gong, L.-K; Ding, K.; Xu, Y.; Wang, R.; Ge, A.; Ren, J.; Li, J.; Li, J.; Ye, Q. J. Med. Chem. 2006, 49, 456; (c) Madan, B.; Singh, I.; Kumar, A.; Prasad, A. K.; Raj, H. G.; Parmar, V. S.; Ghosh, B. Bioorg. Med. Chem. 2002, 10, 3431; (d) Messori, L.; Piccioli, F.; Gabrielli, S.; Orioli, P.; Angeloni, L.; Bugno, C. D. Bioorg. Med. Chem. 2002, 10, 3425; (e) O'Keefe, B. M.; Simmons, N.; Martin, S. F. Org. Lett. 2008, 10, 5301.
[2] Olah, G. A. Friedel-Crafts Chemistry, Wiley, New York, 1973.
[3] (a) Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302; (b) Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551; (c) Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987; (d) Shimizu, H.; Murakami, M. Chem. Commun. 2007, 2855; (e) Wong, Y.-C.; Parthasarathy, K.; Cheng, C.-H. Org. Lett. 2010, 12, 1736; (f) Tsui, G. C.; Glenadel, Q.; Lau, C.; Lautens, M. Org. Lett. 2011, 13, 208; (g) Miao, T.; Wang, G.-W. Chem. Commun. 2011, 47, 9501; (h) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
[4] (a) Fang, P.; Li, M.; Ge, H. J. Am. Chem. Soc. 2010, 132, 11898; (b) Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Lett. 2012, 14, 4358; (c) Wu, Y.; Li, B.; Mao, F.; Li, X.; Kwong, F. Y. Org. Lett. 2011, 13, 3258; (d) Li, C.; Wang, L.; Li, P.; Zhou, W. Chem. Eur. J. 2011, 17, 10208.
[5] (a) Jia, X.; Zhang, S.; Wang, W.; Luo, F.; Cheng, J. Org. Lett. 2009, 11, 3120; (b) Baslé, O.; Bidange, J.; Shuai Q.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1145; (c) Li, M.; Ge, H. Org. Lett. 2010, 12, 3464. (d) Zhou, W.; Li, H.; Wang, L. Org. Lett. 2012, 14, 4594; (e) Xiao, F.; Shuai, Q.; Zhao, F.; Baslé, O.; Deng, G.; Li, C.-J. Org. Lett. 2011, 13, 1614.
[6] Chan, C.-W.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 3926.
[7] (a) Guin, S.; Rout, S. K.; Banerjee, A.; Nandi, S.; Patel, B. K. Org. Lett. 2012, 14, 5294; (b) Yin, Z.; Sun, P. J. Org. Chem. 2012, 77, 11339; (c) Wu, Y.; Choy, P. Y.; Mao, F.; Kwong, F. Y. Chem. Commun. 2013, 49, 689.
[8] Wang, S.; Yang, Z.; Liu, J.; Xie, K.; Wang, A.; Chen, X.; Tan, Z. Chem. Commun. 2012, 48, 9924.
[9] (a) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048; (b) Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2008, 130, 3304; (c) Yu, W.-Y.; Sit, W. N.; Zhou, Z.; Chan, A. S.-C. Org. Lett. 2009, 11, 3174; (d) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679. (潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
[10] Sun, C.-L.; Liu, N.; Li, B.-J.; Yu, D.-G.; Wang, Y.; Shi, Z.-J. Org. Lett. 2010, 12, 184.
[11] Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466.
[12] (a) Ruan, J.; Saidi, O.; Lggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510; (b) álvarez-Bercedo, P.; Flores-Gaspar, A.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2010, 132, 466; (c) Colbon, P.; Ruan, J.; Purdie, M.; Xiao, J. Org. Lett. 2010, 12, 3670; (d) Xia, M.; Chen, Z. Synth. Commun. 2000, 30, 531.
[13] (a) Gooβen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043; (b) Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738; (c) Shang, R.; Liu, L. Sci. China, Chem. 2011, 54, 1670; (d) Li, M.; Wang, C.; Ge, H. Org. Lett. 2011, 13, 2062; (e) Li, M.; Wang, C.; Fang, P.; Ge, H. Chem. Commun. 2011, 47, 6587.
[14] (a) Wang, G.-W.; Yuan, T.-T.; Wu, X.-L. J. Org. Chem. 2008, 73, 4717; (b) Zhu, B.; Wang, G.-W. Org. Lett. 2009, 11, 4334;(c) Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476; (d) Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380; (e) Li, D.-D.; Yuan, T.-T.; Wang, G.-W. Chem. Commun. 2011, 47, 12789; (f) Li, D.-D.; Yuan, T.-T.; Wang, G.-W. J. Org. Chem. 2012, 77, 3341; (g) Su, Y.-T.; Wang, Y.-L.; Wang, G.-W. Chem. Commun. 2012, 48, 8132; (h) Li, F.; Liu, T.-X.; Wang, G.-W. Org. Lett. 2012, 14, 2176; (i) Jiang, T.-S.; Wang, G.-W. J. Org. Chem. 2012, 77, 9504; (j) Jiang, T.-S.; Wang, G.-W. Org. Lett. 2013, 15, 788.
[15] During the preparation of our manuscript, two completely independent works on the Pd-catalyzed reaction of decarboxylative acylation of O-methyl oximes with α-keto acids under different reaction conditions just appeared: (a) Kim, M.; Park, J.; Sharma, S.; Kim, A.; Park, E.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Chem. Commun. 2013, 49, 925; (b) Yang, Z.; Chen, X.; Liu, J.; Gui, Q.; Xie, K.; Li, M.; Tan, Z. Chem. Commun. 2013, 49, 1560.
[16] (a) Fontana, F.; Minisci, F.; Barbosa, M. C. N.; Vismara, E. J. Org. Chem. 1991, 56, 2866; (b) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
[17] Tsai, C.; de Lijser, H. J. P. J. Org. Chem. 2004, 69, 3057.
[18] Wadhwa, K.; Yang, C.; West, P. R.; Deming, K. C.; Chemburkar, S. R.; Reddy, R. E. Synth. Commun. 2008, 38, 4434.

钯催化下肟醚导向的sp² C—H键邻位酰氧化反应

Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp² C—H Bond Activation

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钯催化下肟醚导向的sp2 C—H键邻位酰氧化反应