PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes

doi:10.1007/s40242-019-8264-9

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (1): 26-32.doi: 10.1007/s40242-019-8264-9

PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes

WEI Ying, ZHENG Xiangping, XIE Xinmiao

Center for Molecular Systems and Organic Devices(CMSOD), Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors, Institute of Advanced Materials(IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, P. R. China

收稿日期:2018-08-23 修回日期:2018-09-07 出版日期:2019-02-01 发布日期:2019-01-30
通讯作者: WEI Ying E-mail:iamywei@njupt.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21602111), the Natural Science Foundation of Jiangsu Province, China(No.BK20150832) and the Scientific Foundation of Nanjing University of Posts and Telecommunications, China (Nos.NUPTSF, NY215078).

PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes

WEI Ying, ZHENG Xiangping, XIE Xinmiao

Center for Molecular Systems and Organic Devices(CMSOD), Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors, Institute of Advanced Materials(IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, P. R. China

Received:2018-08-23 Revised:2018-09-07 Online:2019-02-01 Published:2019-01-30
Contact: WEI Ying E-mail:iamywei@njupt.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21602111), the Natural Science Foundation of Jiangsu Province, China(No.BK20150832) and the Scientific Foundation of Nanjing University of Posts and Telecommunications, China (Nos.NUPTSF, NY215078).

摘要/Abstract

摘要： A facile and efficient method for the preparation of methyl ketones was developed in the reaction of alkynes and alkenes with PhIO-BF₃·Et₂O. The reaction features mild conditions, short time and metal-free catalyst. The possible mechanism for the formation of methyl ketones was proposed. H₂O functions as both a nucleophile and an oxygen source.

关键词: Alkyne, Alkene, Ketone, Hydration reaction

Abstract: A facile and efficient method for the preparation of methyl ketones was developed in the reaction of alkynes and alkenes with PhIO-BF₃·Et₂O. The reaction features mild conditions, short time and metal-free catalyst. The possible mechanism for the formation of methyl ketones was proposed. H₂O functions as both a nucleophile and an oxygen source.

Key words: Alkyne, Alkene, Ketone, Hydration reaction

WEI Ying, ZHENG Xiangping, XIE Xinmiao. PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes[J]. 高等学校化学研究, 2019, 35(1): 26-32.

WEI Ying, ZHENG Xiangping, XIE Xinmiao. PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes[J]. Chemical Research in Chinese Universities, 2019, 35(1): 26-32.

参考文献

[1] Alonso F., Beletskaya I. P., Yus M., Chem. Rev., 2004, 104, 3079
[2] Hintermann L., Labonne A., Synthesis, 2007, 1121
[3] Kutscheroff M., Chem. Ber., 1884, 17, 13
[4] Nishizawa M., Skwarczynski M., Imagawa H., Sugihara T., Chem. Lett., 2002, 31, 12
[5] Ghosh N., Nayak S., Sahoo A. K., J. Org. Chem., 2011, 76, 500
[6] Wang D., Cai R., Sharma S., Jirak J., Thummanapelli S. K., Akhmedov N. G., Zhang H., Liu X., Petersen J. L., Shi X., J. Am. Chem. Soc., 2012, 134, 9012
[7] Hiscox W., Jennings P. W., Organometallics, 1990, 9, 1997
[8] Jennings P. W., Hartman J. W., Hiscox W. C., Inorg. Chim. Acta, 1994, 222, 317
[9] Wu X. F., Bezier D., Darcel C., Adv. Synth. Catal., 2009, 351, 367
[10] McDonald R. I., Liu G., Stahl S. S., Chem. Rev., 2011, 111, 2981
[11] Mitsudome T., Yoshida S., Mizugaki T., Jitsukawa K., Kaneda K., Angew. Chem. Int. Ed., 2013, 52, 5961
[12] Hirabayashi T., Okimoto Y., Saito A., Morita M., Sakaguchi S., Ishii Y., Tetrahedron, 2006, 62, 2231
[13] Thuong M. B. T., Mann A., Wagner A., Chem. Commun., 2012, 48, 434
[14] Jin X., Oishi, T., Yamaguchi K., Mizuno N., Chem. Eur. J., 2011, 17, 1261
[15] Harman W. D., Dobson J. C., Taube H., J. Am. Chem. Soc., 1989, 111, 3061
[16] Tachinami T., Nishimura T., Ushimaru R., Noyori R., Naka H., J. Am. Chem. Soc., 2013, 135, 50
[17] Hintermann L., Labonne A., Synthesis, 2007, 1121
[18] Ibrahim N., Vilhelmsen M. H., Pernpointner M., Rominger F., Hashmi A. S. K., Organometallics, 2013, 32, 2576
[19] Zhdankin V. V., J. Org. Chem., 2011, 76, 1185
[20] Yoshimura A., Zhdankin V. V., Chem. Rev., 2016, 116, 3328
[21] Wang X., Studer A., Acc. Chem. Res., 2017, 50, 1712
[22] Mo D. L., Dai L. X., Hou X. L., Tetrahedron Lett., 2009, 50, 5578
[23] Barluenga J., Lonzi G., Riesgo L., Miguel Tomás López L. A., J. Am. Chem. Soc., 2011, 133, 18138
[24] He Z., Zhang R., Hu M., Li L., Ni C., Hu J., Chem. Sci., 2013, 4, 3478
[25] Sohmiya H., Kimura T., Bauchat P., Fujita M., Ando T., Chem. Lett., 1991, 1391
[26] Wang L., Li P., Yan J., Wu Z., Tetrahedron Lett., 2003, 44, 4685
[27] Haddach M., McCarthy J. R., Tetrahedron Lett., 1999, 40, 3109
[28] Trécourt F., Breton G., Bonnet V., Mongin F., Marsais F., Quéguiner G., Tetrahedron, 2000, 56, 1349
[29] Xu C. F., Xu M., Jia Y. X., Li C. Y., Org. Lett., 2011, 13, 1556
[30] Chikashita H., Ide H., Itoh K., J. Org. Chem., 1986, 51, 5400
[31] Zhou C. Y., Chan P. W. H., Che C. M., Org. Lett., 2006, 8, 325
[32] Xia Y., Qu S., Xiao Q., Wang Z. X., Qu P., Chen L., Liu Z., Tian L., Huang Z., Zhang Y., Wang J., J. Am. Chem. Soc., 2013, 135, 13502
[33] Sniady A., Wheeler K. A., Dembinski R., Org. Lett., 2005, 7, 1769
[34] Brown R. C. D., Angew. Chem., Int. Ed., 2005, 44, 850
[35] Ochiai M., Miyamoto K., Yokota Y., Suefuji T., Shiro M., Angew. Chem., Int. Ed., 2005, 44, 75
[36] Miyamoto K., Tada N., Ochiai M., J. Am. Chem. Soc., 2007, 129, 2772
[37] Souto J. A., Becker P., Iglesias Á., Muñiz K., J. Am. Chem. Soc., 2012, 134, 15505
[38] Saito A., Taniguchi A., Kambara Y., Hanzawa Y., Org. Lett., 2013, 15, 2672
[39] Tokunaga M., Suzuki T., Koga N., Fukushima T., Horiuchi A., Wakatsuki Y., J. Am. Chem. Soc., 2001, 123, 11917
[40] Brenzovich Jr. W. E., Angew. Chem. Int. Ed., 2012, 51, 8933
[41] Rao K. T. V., Prasad P. S. S., Lingaiah N., Green Chem., 2012, 14, 1507
[42] Ochiai M., Sumi K., Nagao Y., Fujita E., Arimoto M., Yamaguchi H., J. Chem. Soc., Chem. Commun., 1985, 697
[43] Sromek A. W., Rubina M., Gevorgyan V., J. Am. Chem. Soc., 2005, 127, 10500

PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes

PhIO-mediated Synthesis of Ketones from Alkynes and Alkenes

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	FANG Yuan, HEYDARI Zahra, LIU Chenghao, ZHANG Nianyue, CUCCIA Louis A., IVASENKO Oleksandr, PEREPICHKA Dmitrii F.. Glaser Coupling of Substituted Anthracene Diynes on a Non-metallic Surface at the Vapor-Solid Interface[J]. 高等学校化学研究, 2021, 37(5): 1143-1148.
[2]	CUI Zengduo, WANG Yongpeng, LIU Mengzhu, ZHANG Haibo, JIANG Zhenhua. Self-cleaning and Oil/Water Separation of 3D Network Super-hydrophobic Bead-like Fluorinated Silica Pellets/Poly(aryl ether ketone) Composite Membrane Fabricated via a Facile One-step Electrospinning[J]. 高等学校化学研究, 2020, 36(6): 1320-1325.
[3]	YU Fengli, CHI Yujie, GAO Chong, CHEN Ruirui, XIE Congxia, YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids[J]. 高等学校化学研究, 2020, 36(5): 865-869.
[4]	LI Ruyue, WU Mingwei, PAN Biwei, LI Meng, HUANG Jun. Aerobic Oxidation of Alcohols to Aldehydes and Ketones with Recyclable Pd Catalysts on Cross-linked 1,10-Phenanthroline Polymers[J]. 高等学校化学研究, 2020, 36(5): 934-939.
[5]	CHEN Zhanguo, WEN Ting, HOU Dan. K₃PO₄-promoted Cyclopropanation of Electron-deficient Alkenes with 2-Bromo-1,3-propanedione Compounds[J]. 高等学校化学研究, 2019, 35(6): 1002-1007.
[6]	ZHAO Qi, LIANG Xiaoxiao, YOU Yingxue, WANG Yuliang, DU Xinwei, LIU Baijun, HU Wei. Proton Conductivity Improvement Effect of Cellulose on SPEEKK Based PEM[J]. 高等学校化学研究, 2019, 35(5): 916-923.
[7]	LIU Zhenchao, WANG Peng, HU Wei, LIU Baijun. Preparation and Properties of Hybrid Silane-crosslinked Sulfonated Poly(aryl ether ketone)s as Proton Exchange Membranes[J]. 高等学校化学研究, 2019, 35(5): 937-944.
[8]	YANG Xue, WEI Yingcong, CHU Xuefeng, ZHAO Qi, YAN Wenling, DONG Chenjun, LIU Baijun, SUN Zhaoyan, HU Wei, ZHANG Niaona. Carboxyl-functionalized Nanocellulose Reinforced Nanocomposite Proton Exchange Membrane[J]. 高等学校化学研究, 2019, 35(4): 735-741.
[9]	LI Jing, LIU Hongwei, MENG Fanyu, YAN Liuqing, SHI Yanpeng, ZHANG Yumin, GU Qiang. Microwave-assisted Synthesis of New 1,2,3-Triazoles Bearing an Isoxazole Ring by the Azide-alkyne Cycloaddition Click Chemistry[J]. 高等学校化学研究, 2018, 34(2): 197-202.
[10]	ZHENG Renhua, HUANG Qing, GUOHaichang, HUANGYidie, JIANG Huajiang. Gold-catalyzed Intermolecular Oxidation of Phenylacetylene and Allylic Sulfides: an Efficient and Practical Synthesis of α-Phenylthio Ketone[J]. 高等学校化学研究, 2018, 34(1): 57-60.
[11]	FAN Chenli, HE Xinwei, LIAO Kaisheng, WANG Cui'e, SHANG Yongjia. 4-Dimethylaminopyridine-catalyzed Cascade Reaction for Efficient Synthesis of Naphthofurans[J]. 高等学校化学研究, 2016, 32(1): 62-67.
[12]	LIU Can, ZHOU Ya, YANG Liwen, YANG Nianfa, ZHANG Anlin. Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone[J]. 高等学校化学研究, 2015, 31(4): 669-673.
[13]	ZENG Ruijie, SHENG Hongting, RAO Bo, FENG Yan, WANG Hao, SUN Yehua, CHEN Man, ZHU Manzhou. An Efficient and Green Approach to Synthesizing Enamines by Intermolecular Hydroamination of Activated Alkynes[J]. 高等学校化学研究, 2015, 31(2): 212-217.
[14]	CHENG Xu, LI Xiaolong, WAN Weili, HAO Wenmei, HAI Li, WU Yong. Indole-tolerant Oxidation of 1,2-Diarylalkynes to 1,2-Diketone Derivatives[J]. 高等学校化学研究, 2015, 31(1): 53-59.
[15]	ZONG Chenglong, ZENG Runsheng, ZOU Jianping. One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions[J]. 高等学校化学研究, 2014, 30(4): 632-638.