I2/离子液体作为可回收均相催化剂在微波条件下高效制备全乙酰糖

doi:10.1016/S1872-2067(14)60219-9

催化学报 ›› 2015, Vol. 36 ›› Issue (2): 237-243.DOI: 10.1016/S1872-2067(14)60219-9

I₂/离子液体作为可回收均相催化剂在微波条件下高效制备全乙酰糖

熊兴泉, 易超, 韩骞, 石霖, 李四中

华侨大学材料科学与工程学院, 福建省高校功能材料重点实验室, 福建厦门361021

收稿日期:2014-06-19 修回日期:2014-08-29 出版日期:2015-01-21 发布日期:2015-01-21
通讯作者: 熊兴泉
基金资助:
国家自然科学基金(21004024); 福建省自然科学基金(2011J01046); 福建省“高校新世纪优秀人才支持计划”(2012FJ- NCET-ZR03); 福建省“高校杰出青年科研人才培育计划”(11FJPY02); 华侨大学中青年教师科研提升资助计划(ZQN-YX103); 福建省青年人才创新项目(2011J05131).

I₂/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation

Xingquan Xiong, Chao Yi, Qian Han, Lin Shi, Sizhong Li

College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, Fujian, China

Received:2014-06-19 Revised:2014-08-29 Online:2015-01-21 Published:2015-01-21
Supported by:
This work was supported by the National Natural Science Foundation of China (21004024), the Natural Science Foundation of Fujian Province (2011J01046), the Program for New Century Excellent Talents in University of Fujian Province (2012FJ-NCET-ZR03), the Promotion Program for Young and Middle-Aged Teachers in Science and Technology Research of Huaqiao University (ZQN-YX103), and the Special Foundation for Young Scientists of Fujian Province (2011J05131).

摘要/Abstract

摘要：

以可回收的I₂/PEG₄₀₀型离子液体(I₂/IL₄₀₀)为催化体系, 发展了一种高效、实用的合成全乙酰糖衍生物的方法. 结果表明, 以糖与乙酸酐为原料, 在微波辐射、无溶剂条件以及I₂/IL₄₀₀体系中, 数分钟之内可以非常高的产率(90%-99%)和数十毫摩尔规模(50.0 mmol)制备出全乙酰糖. 通过简单的甲苯萃取, 可以从I₂/IL₄₀₀体系中分离出全乙酰糖, I₂/IL₄₀₀体系可循环使用6次, 且产率均在90%以上. 当反应规模扩大到50.0 mmol时, 该体系依然能高效快速地催化糖的全乙酰化, 并且可以循环使用5次, 产率依然维持在90%左右.

关键词: 全乙酰糖, 碘, 离子液体, 微波辐射

Abstract:

A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG₄₀₀-based ionic liquid catalyst (I₂/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I₂/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.

Key words: Peracetylated sugar, Iodine, Ionic liquid, Microwave irradiation

熊兴泉, 易超, 韩骞, 石霖, 李四中. I₂/离子液体作为可回收均相催化剂在微波条件下高效制备全乙酰糖[J]. 催化学报, 2015, 36(2): 237-243.

Xingquan Xiong, Chao Yi, Qian Han, Lin Shi, Sizhong Li. I₂/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation[J]. Chinese Journal of Catalysis, 2015, 36(2): 237-243.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60219-9

https://www.cjcatal.com/CN/Y2015/V36/I2/237

参考文献

[1] Collins P C, Ferrier R J. Monosaccharides: Their Chemistry and Their Roles in Natural Products. New York: John Wiley & Sons, 1995. 360
[2] Garegg P J. Acc Chem Res, 1992, 25: 575
[3] Kunz H. Angew Chem Int Ed, 1987, 26: 294
[4] Dwek R A. Chem Rev, 1996, 96: 683
[5] Nicolaou K C, Mitchell H J. Angew Chem Int Ed, 2001, 40: 1576
[6] Davis B G. Chem Rev, 2002, 102: 579
[7] Toshima K, Tatsuta K. Chem Rev, 1993, 93: 1503
[8] Ye X S, Wong C H. J Org Chem, 2000, 65: 2410
[9] Li B, Zeng Y, Hauser S, Song H J, Wang L X. J Am Chem Soc, 2005, 127: 9692
[10] Wang Q B, Fu J, Zhang J B. Carbohydr Res, 2008, 343: 2989
[11] Wolfrom M L, Thompson A. In: Whistler R L, Wolfrom M L, BeMiller J N, eds. Methods in Carbohydrate Chemistry. Vol. 2. New York: Academic Press, 1963. 211
[12] Cohen R B, Tsou K C, Rutenburg S H, Seligman A M. J Biol Chem, 1952, 195: 239
[13] Hyatt J A, Tindall G W. Heterocycles, 1993, 35: 227
[14] Vogel A I. Vogel's Textbook of Practical Organic Chemistry. 5th Ed. New York: Wiley, 1989. 644
[15] Das S K, Reddy K A, Krovvidi V L N R, Mukkanti K. Carbohydr Res, 2005, 340: 1387
[16] Bizier N P, Atkins S R, Helland L C, Colvin S F, Twitchell J R, Cloninger M J. Carbohydr Res, 2008, 343: 1814
[17] Limousin C, Cleophax J, Petit A, Loupy A, Lukacs G. J Carbohydr Chem, 1997, 16: 327
[18] Shi L, Zhang G S, Pan F. Tetrahedron, 2008, 64: 2572
[19] Dasgupta F, Singh P P, Srivastava H C. Carbohydr Res, 1980, 80: 346
[20] Orita A, Tanahashi C, Kakuda A, Otera J. J Org Chem, 2001, 66: 8926
[21] Lee J C, Tai C A, Hung S C. Tetrahedron Lett, 2002, 43: 851
[22] Procopiou P A, Baugh S P D, Flack S S, Inglis G G A. J Org Chem, 1998, 63: 2342
[23] Tai C A, Kulkarni S S, Hung S C. J Org Chem, 2003, 68: 8719
[24] Bartoli G, Dalpozzo R, De Nino A, Maiuolo L, Nardi M, Procopio A, Tagarelli A. Green Chem, 2004, 6: 191
[25] Agnihotri G, Tiwari P, Misra A K. Carbohydr Res, 2005, 340: 1393
[26] Wu H, Shen Y, Fan L Y, Wan Y, Shi D Q. Tetrahedron, 2006, 62: 7995
[27] Mukhopadhyay B, Russell D A, Field R A. Carbohydr Res, 2005, 340: 1075
[28] Misra A K, Tiwari P, Madhusudan S K. Carbohydr Res, 2005, 340: 325
[29] Wu L Q, Yin Z K. Carbohydr Res, 2013, 365: 14
[30] Zhang J B, Zhang B, Zhou J F, Li J, Shi C J, Huang T, Wang Z F, Tang J. J Carbohydr Chem, 2011, 30: 165
[31] Zhou Y, Yan P F, Li G M, Chen Z J. Chin J Org Chem (周颖, 闫鹏飞, 李光明, 陈正军. 有机化学), 2009, 29: 1719
[32] Kartha K P R, Field R A. Tetrahedron, 1997, 53: 11753
[33] Mingos D M P, Whittaker A G. In: van Eldik R, Hubbard C D, eds. Microwave Dielectric Heating Effects in Chemical Synthesis in Chemistry under Extreme or Nonclassical Conditions. New York: John Wiley & Sons, 1997. 479
[34] Loupy A. Microwaves in Organic Synthesis. Weinheim: Wiley-VCH, 2002
[35] Hayes B L. Microwave Synthesis: Chemistry at the Speed of Light. Matthews, NC: CEM Publishing, 2002
[36] Varma R S. Microwave Technology—Chemical Synthesis Applications: Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley & Sons, 2003
[37] Lidstrom P, Tierney J, Wathey B, Westman J. Tetrahedron, 2001, 57: 9225
[38] De la Hoz A, Díaz-Ortiz Á, Moreno A. Chem Soc Rev, 2005, 34: 164
[39] Xiong X Q, Cai L, Tang Z K. Chin J Org Chem (熊兴泉, 蔡雷, 唐忠科. 有机化学), 2012, 32: 1410
[40] Xiong X Q, Cai L. Catal Sci Technol, 2013, 3: 1301
[41] Xiong X Q, Chen H X, Tang Z K, Jiang Y B. RSC Adv, 2014, 4: 9830
[42] Xiong X Q, Cai L, Jiang Y B, Han Q. ACS Sustainable Chem Eng, 2014, 2: 765
[43] Xiong X Q, Chen H X, Zhu R J. Catal Commun, 2014, 54: 94

I₂/离子液体作为可回收均相催化剂在微波条件下高效制备全乙酰糖

I₂/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	顾幸威, 张有灿, 赵丰乾, 艾汉均, 吴小锋. 膦催化光促进的烷基碘和苯酚及1,4-二氧六环的以电子转移化合物为媒介的羰基化酯化反应[J]. 催化学报, 2023, 48(5): 214-223.
[2]	Ernest Pahuyo Delmo, 王忆安, 王菁, 朱尚乾, 李铁怀, 秦雪苹, 田一博, 赵青蓝, Juhee Jang, 王一诺, 谷猛, 张莉莉, 邵敏华. 金属有机框架-离子液体混合催化剂用于电化学还原二氧化碳生成甲烷[J]. 催化学报, 2022, 43(7): 1687-1696.
[3]	于子勋, 刘畅, 邓业煜, 李默涵, 厍芳馨, Leo Lai, 陈元, 魏力. 利用离子液体界面工程实现非均相分子催化剂高效生产双氧水[J]. 催化学报, 2022, 43(5): 1238-1246.
[4]	任亦起, 陶琳, 李纯志, Sanjeevi Jayakumar, 李贺, 杨启华. 喹啉及其衍生物的多相不对称氢转移反应[J]. 催化学报, 2021, 42(9): 1576-1585.
[5]	陈必华, 丁桐, 邓熹, 王鑫, 张大卫, 马三罐, 张永亚, 倪兵, 高国华. 酸性聚离子液体溶胀诱导自组装形成类蜂窝状固体酸催化剂及其高效催化水解反应[J]. 催化学报, 2021, 42(2): 297-309.
[6]	赵佳, 王赛赛, 王柏林, 岳玉学, 金春晓, 陆金跃, 方正, 庞祥雪, 丰枫, 郭伶伶, 潘志彦, 李小年. 乙炔氢氯化反应中的负载金-离子液体催化剂: 离子态金物种的稳定机制[J]. 催化学报, 2021, 42(2): 334-346.
[7]	李凯, 季梦夏, 陈蓉, 姜琪, 夏杰祥, 李华明. 氮磷共掺杂石墨烯量子点/Bi₅O₇I复合材料的构筑及增强的光催化降解性能[J]. 催化学报, 2020, 41(8): 1230-1239.
[8]	郑光范, 孙佳琼, 许有伟, 周旭凯, 高辉, 李兴伟. Rh(III)催化基于胺化试剂极性翻转策略的定位基辅助芳烃C-H键胺化反应[J]. 催化学报, 2020, 41(11): 1723-1733.
[9]	汪圣尧, 熊中亮, 杨楠, 丁星, 陈浩. 基于钼酸铋的碘掺杂辅助氧空位可控引入及其高效活化分子氧和矿化五氯酚作用[J]. 催化学报, 2020, 41(10): 1544-1553.
[10]	李明浩, 吴丰田, 顾彦龙. Brönsted酸性离子液体催化α-羟基丙酮和2-苯基吲哚反应合成苯并[a]咔唑[J]. 催化学报, 2019, 40(8): 1135-1140.
[11]	陈翰祥, 曾洁, 陈敏东, 陈志刚, 季梦夏, 赵君泽, 夏杰祥, 李华明. 反应型离子液体辅助合成钒酸铁介孔纳米棒及其增强可见光光催化活性[J]. 催化学报, 2019, 40(5): 744-754.
[12]	王国芹, 宋河远, 李瑞云, 李臻, 陈静. 新型高效Brönsted酸性离子液体催化剂体系催化烯烃齐聚反应[J]. 催化学报, 2018, 39(6): 1110-1120.
[13]	付西英, 谢鹏涛, 连一苇, 何乐芹, 赵伟, 常涛, 秦身钧. 基于两性离子型季铵盐-KI的温度控制自分离离子液体(IL)催化体系用于二氧化碳固定反应[J]. 催化学报, 2018, 39(11): 1854-1860.
[14]	李赫楠, 徐雅楠, Hansinee Sitinamaluwa, Kimal Wasalathilake, Dilini Galpaya, 闫澄. 石墨化氮化碳负载Cu纳米颗粒用作高效氧还原电催化剂[J]. 催化学报, 2017, 38(6): 1006-1010.
[15]	张伟, 韩峰, 童进, 夏春谷, 刘建华. 1,1,3,3-四烷基胍羰基钴离子液体:高效可循环利用的环氧化合物羰基化反应催化新材料[J]. 催化学报, 2017, 38(5): 805-812.