镍催化烷基羧酸与对甲苯磺酸甲酯还原偶联甲基化成酮反应
收稿日期: 2017-03-24
修回日期: 2017-04-16
网络出版日期: 2017-05-17
基金资助
国家自然科学基金（No.61204020）和上海市教委创新（No.15ZZ047）资助项目.
Nickel-Catalyzed Reductive Methylation of Alkyl Acid with Methyl p-Tosylate
Received date: 2017-03-24
Revised date: 2017-04-16
Online published: 2017-05-17
Supported by
Project supported by the National Natural Science Foundation of China (No.61204020) and the Innovation Program of Shanghai Municipal Education Commission (No.15ZZ047).
顾君 , 刘建东 , 孙雨人 , 王洪宇 . 镍催化烷基羧酸与对甲苯磺酸甲酯还原偶联甲基化成酮反应[J]. 有机化学, 2017 , 37(7) : 1830 -1834 . DOI: 10.6023/cjoc201703042
Methyl group is the smallest carbon substituent that plays important roles in many compounds. Conversion of a carboxylic acid into a ketone is a fundamental transformation in organic chemistry. This functional group change is usually performed indirectly by activating the carboxylic acid into an acyl chloride or into a Weinreb amide, and then by nucleophilic attack with an organometallic reagent. However, direct conversion of a carboxylic acid into a ketone can be achieved in one-step reaction using at least 2 equiv. of an organolithium reagent at low temperature and producing much tertiary alcohol. Herein, methylation of alkyl acid under Ni-catalyzed reductive coupling conditions using methyl p-methyl tosylate as the methylation reagent was reported to yield methylated ketones. Moderate yields as well as good functional group tolerance were observed under the present mild and easy-to-operate reaction conditions.
Key words： methylation; nickel-catalyzed; alkyl acid; reductive coupling
[1] Sheng, W.; Jin, C.; Shan, S.; Jia, Y.; Gao, J. Chin. J. Org. Chem. 2016, 36, 325(in Chinese). (盛卫坚, 金城安, 单尚, 贾义霞, 高建荣, 有机化学, 2016, 36, 325.)
[2] Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90(in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
[3] Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66(in Chinese). (苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.)
[4] Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽,匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.)
[5] Zhuang, H.; Zeng, R.; Zou, J. Chin. J. Org. Chem. 2016, 34, 368.
[6] Heike, S.; Tim, C. Angew. Chem., Int. Ed. 2013, 52, 2.
[7] Barreiro, E. J.; Kümmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215.
[8] Peretti, K. L.; Ajiro, H.; Cohen, C. T.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11566.
[9] Nicholson, J. W.; Wilson, A. D. J. Chem. Educ. 2004, 81, 1362.
[10] Wilkinson, M. C. Org. Lett. 2011, 13, 2232.
[11] Park, A.; Park, K.; Kim, Y.; Lee, S. Org. Lett. 2011, 13, 944.
[12] Gooβen, L.; Rodriguez, N.; Gooβen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
[13] Posner, G. H.; Whitten, C. E.; McFarland, P. E. J. Am. Chem. Soc. 1972, 94, 5106.
[14] Wang, X.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593.
[15] Ryu, I.; Ikebe, M.; Sonoda, N.; Yamato, S.; Yamamura, G.; Komatsu, M. Tetrahedron Lett. 2002, 43, 1257.
[16] Dieter, R. K. Tetrahedron 1999, 55, 4177.
[17] Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
[18] Kangani, C. O.; Kelley, D. E.; Day, B. W. Tetrahedron Lett. 2006, 6289.
[19] Qu, B.; Collum, D. B. J. Org. Chem. 2006, 71, 7117.
[20] Alonso, F.; Lorenzo, E.; Yus, M. J. Org. Chem. 1996, 61, 6058.
[21] Gilman, H.; van Ess, P. R. J. Am. Chem. Soc. 1933, 55, 1258.
[22] Tegner, C. Acta Chem. Scand 1952, 6, 782.
[23] Jorgenson, M. J. Org. React. 1970, 18, 1.
[24] Bare, T. M.; House, H. O. Org. Synth. 1973, 5, 775.
[25] Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1988, 110, 7447
[26] (a) Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411.
(b) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793.
(c) Knappke, C. E.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem. Eur. J. 2014, 20, 6828.
(d) Weix, D. J. Acc. Chem. Res. 2015, 48, 1767.
(e) Moragas, T.; Correa, A.; Martin, R. Chem. Eur. J. 2014, 20, 8242.
(f) Wang, X.; Dai, Y.; Gong, H. Top. Curr. Chem. 2016, 374, 43.
[27] Fillon, F.; Gosmini, C.; Perichon, J. Tetrahedron 2003, 59, 8199.
[28] Hsieh, J.-H.; Cheng, C.-H. Chem. Commun. 2005, 4554.
[29] Wotal, A.; Weix, D. J. Org. Lett. 2012, 14, 1476.
[30] Wu, F.; Gong, H. Org. Lett. 2012, 14, 3044.
[31] Yin, H.; Zhao, C.; You, H.; Lin, Q.; Gong, H. Chem. Commun. 2012, 48, 7034.
[32] Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2013, 136, 17645.
[33] Lu, W.; Liang, Z.; Zhang, Y.; Wu, F.; Qian, Q.; Gong, H. Synthesis 2013, 45, 2234.
[34] Liang, Z.; Xue, W.; Lin, K.; Gong, H. Org. Lett. 2014, 16, 5620.
[35] Jia, X.; Zhang, X.; Qian, Q.; Gong, H. Chem. Commun. 2015, 51, 10302.
[36] Christelle, P.; François, C.; Bertrand, C. Org. Lett. 2001, 3, 803.
/
| 〈 |
|
〉 |
