碱土金属促进氢官能团化反应的研究进展

doi:10.6023/cjoc201804031

有机化学 ›› 2018, Vol. 38 ›› Issue (8): 1885-1896.DOI: 10.6023/cjoc201804031 上一篇下一篇

所属专题：碳氢活化合辑2018-2019；元素有机化学合辑2018-2019

综述与进展

碱土金属促进氢官能团化反应的研究进展

李园园^a,b,d, 程玉华^a, 单春晖^c, 张敬^e, 徐冬冬^c, 白若鹏^c, 屈凌波^d, 蓝宇^c,d

a 重庆第二师范学院生物与化学工程学院重庆 400067;
b 重庆第二师范学院脂质资源与儿童日化品协同创新中心重庆 400067;
c 重庆大学化学化工学院重庆 401331;
d 郑州大学化学与分子工程学院郑州 450006;
e 济宁学院化学与化工系济宁 272001

收稿日期:2018-04-16 修回日期:2018-05-11 发布日期:2018-05-17
通讯作者: 蓝宇 E-mail:lanyu@cqu.edu.cn
基金资助:
重庆市科委基金（基础研究与前沿探索）（No.cstc2017jcyjAX0371）、重庆第二师范学院科技协同创新平台建设（No.2017XJPT01）、重庆第二师范学院校级重点项目（No.KY201704A）及重庆第二师范学院博士启动基金（No.2017BSRC001）资助项目.

Recent Advances in Alkaline-Earth-Metal-Catalyzed Hydrofunctionalization Reactions

Li Yuanyuan^a,b,d, Cheng Yuhua^a, Shan Chunhui^c, Zhang Jing^e, Xu Dongdong^c, Bai Ruopeng^c, Qu Lingbo^d, Lan Yu^c,d

a College of Biological and Chemical Engineering, Chongqing University of Education, Chongqing 400067;
b Cooperative Innovation Center of Lipid Resources and Children's Daily Chemicals, Chongqing University of Education, Chongqing 400067;
c School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 401331;
d College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450006;
e Department of Chemistry and Chemical Engineering, Jining University, Jining 272001

Received:2018-04-16 Revised:2018-05-11 Published:2018-05-17
Contact: 10.6023/cjoc201804031 E-mail:lanyu@cqu.edu.cn
Supported by:
Project supported by the Basic and Frontier Research Project of Chongqing Science and Technology Commission (No. cstc2017jcyjAX0371), the Project of Science and Technology Collaborative Innovation Platform Construction of Chongqing University of Education (No. 2017XJPT01), the University-level Key Projects of Chongqing University of Education (No. KY201704A), and the Scientific Research Foundation of Chongqing University of Education (No. 2017BSRC001).

文章分享

摘要/Abstract

碱土金属及其化合物由于其储量丰富、成本低而被应用于催化反应中.近年来，碱土金属催化脱氢偶联反应、硼氢化反应、氢膦化反应、氢胺化反应以及氢化硅烷化反应等被关注和研究，无论在实验还是原理上都取得了大量的进展.针对这类反应及其机理进行总结归纳，从而完整描绘了碱土金属在氢化或脱氢反应中起到的作用.这类反应中，往往都涉及到碱土金属氢化物作为活性物种，反应过程中都要经历碱土金属氢共价键的形成和断裂.通过对这些反应的分类和讨论，从整体上认识了这类反应的反应条件和反应历程，为今后设计碱土金属催化剂和同类型反应的催化循环提供了指导.

关键词: 碱土金属催化剂, 氢官能团化反应, 机理研究, 研究进展

Alkaline-earth-metal compounds have been widely concerned due to its abundant reserve and the low-cost. In recent years, alkaline-earth-metal catalysis has achieved great progress in dehydrocoupling, hydroboration, hydrophosphination, hydroamination, hydrosilylation reactions experimentally and therotically. These types of reaction and catalytic mechanism, leading to indentify the role of alkaline-earth-metal in hydrogenation and dehydrogenation reaction are summarized. These reactions, in which the metal-hydride act as active species, generally undergo the reaction pathway involving the cleavage and formation of the metal-hydride covalent bond. The reaction features and mechanisms are generally recognized accrossing to the classification and discussion of these reactions, which would provide guidance for further development of alkaline-earth-metal catalysis.

Key words: alkaline-earth-metals catalyst, hydrofunctionalization reaction, mechanism study, recent advance

引用此文

李园园, 程玉华, 单春晖, 张敬, 徐冬冬, 白若鹏, 屈凌波, 蓝宇. 碱土金属促进氢官能团化反应的研究进展[J]. 有机化学, 2018, 38(8): 1885-1896.

Li Yuanyuan, Cheng Yuhua, Shan Chunhui, Zhang Jing, Xu Dongdong, Bai Ruopeng, Qu Lingbo, Lan Yu. Recent Advances in Alkaline-Earth-Metal-Catalyzed Hydrofunctionalization Reactions[J]. Chin. J. Org. Chem., 2018, 38(8): 1885-1896.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Stephan, D. W. J. Am. Chem. Soc. 2015, 137, 10018.
[2] Qi, X. T.; Liu, S.; Zhang, T.; Long, R.; Huang, J.; Gong, J. X.; Yang, Z.; Lan, Y. J. Org. Chem. 2016, 81, 8306.
[3] Qi, X. T.; Li, Y. Z.; Bai, R. P.; Lan, Y. Acc. Chem. Res. 2017, 50, 2799.
[4] Cui, C. X.; Zhang, Z. P.; Zhu, L.; Qu, L. B.; Zhang, Y. P.; Lan, Y. Phys. Chem. Chem. Phys. 2017, 19, 30393.
[5] Li, Y. Z.; Zou, L. F.; Bai, R. P.; Lan, Y. Org. Chem. Front. 2018, 5, 615.
[6] Zhu, L.; Ye, J. H.; Duan, M.; Qi, X. T.; Yu, D. G.; Bai, R. P.; Lan, Y. Org. Chem. Front. 2018, 5, 633.
[7] Yue, X. Y.; Shan, C. H.; Qi, X. T.; Luo, X. L.; Zhu, L.; Zhang, T.; Li, Y. Y.; Li, Y. Z.; Bai, R. P.; Lan, Y. Dalton Trans. 2018, 47, 1819.
[8] Luo, Y. X.; Liu, S.; Xu, D. D.; Qu, L. B.; Luo, X. L.; Bai, R. P.; Lan, Y. J. Organomet. Chem. 2018, 1.
[9] Qi, X. T.; Liu, X. F.; Qu, L. B.; Liu, Q.; Lan, Y. J. Catal. 2018, 362, 25.
[10] Cui, C. X.; Shan, C. H.; Zhang, Y. P.; Chen, X. T.; Qu, L. B.; Lan, Y. Chem.-Asian J. 2018, 3, 30.
[11] Liu, S.; Qi, X. T.; Qu, L. B.; Bai, R. P.; Lan, Y. Catal. Sci. Technol. 2018, 8, 1645.
[12] Yaroshevsky, A. Geochem. Int. 2006, 44, 48.
[13] Green, S. P.; Jones, C.; Stasch, A. Science 2007, 318, 1754.
[14] Rossin, A.; Peruzzini, M. Chem. Rev. 2016, 116, 8848.
[15] Krieck, S.; Görls, H.; Yu, L.; Reiher, M.; Westerhausen, M. J. Am. Chem. Soc. 2009, 131, 2977.
[16] Westerhausen, M. Angew. Chem., Int. Ed. 2008, 47, 2185.
[17] Hill, M. S.; Liptrot, D. J.; Weetman, C. Chem. Soc. Rev. 2016, 45, 972.
[18] Rochat, R.; Lopez, M. J.; Tsurugi, H.; Mashima, K. ChemCatChem 2016, 8, 10.
[19] Ma, M. T.; Wang, W. F.; Yao, W. W. Chin. J. Org. Chem. 2016, 36, 72(in Chinese). (马猛涛, 王未凡, 姚薇薇, 有机化学, 2016, 36, 72.)
[20] Li, Y. W.; Marks, T. J. Organometallics 1996, 15, 3770.
[21] Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
[22] Hong, S. W.; Tian, S. M.; Metz, V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768.
[23] Wobser, S. D.; Stephenson, C. J.; Delferro, M.; Marks, T. J. Organometallics 2013, 32, 1317.
[24] Seo, S.; Yu, X. H.; Marks, T. J. Tetrahedron Lett. 2013, 54, 1828.
[25] Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111.
[26] Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091.
[27] Stubbert, B. D.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 4253.
[28] Yu, X. H.; Seo, S.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7244.
[29] Dzudza, A.; Marks, T. J. Org. Lett. 2009, 11, 1523.
[30] Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486.
[31] Motta, A.; Fragala, I. L. Marks, T. J. Organometallics 2005, 24, 4995.
[32] Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. Organometallics 2003, 22, 4630.
[33] Seo, S. Y.; Yu X. H.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 263.
[34] Hong, S.; Kawaoka, A. M., Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878.
[35] Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
[36] Weiss, C. J.; Wobser, S. D.; Marks, T. J. Organometallics 2010, 29, 6308.
[37] Liptrot, D. J.; Hill, M. S.; Mahon, M. F.; Wilson, A. S. S. Angew. Chem., Int. Ed. 2015, 54, 13362.
[38] Xu, D. D.; Shan, C. H.; Li, Y. Z.; Qi, X. T.; Luo, X. L.; Bai, R. P.; Lan, Y. Inorg. Chem. Front. 2017, 4, 1813.
[39] Lampland, N. L.; Hovey, M.; Mukherjee, D.; Sadow, A. D. ACS Catal. 2015, 5, 4219.
[40] Arrowsmith, M.; Hill, M. S.; Kociok-Kohn, G. Chem.-Eur. J. 2013, 19, 2776.
[41] Arrowsmith, M.; Hadlington, T. J.; Hill, M. S.; Kociok-Kohn, G. Chem. Commun. 2012, 48, 4567.
[42] Weetman, C.; Anker, M. D.; Arrowsmith, M.; Hill, M. S.; Ko-ciok-Köhn, G.; Liptrot, D. J.; Mahon, M. F. Chem. Sci. 2016, 7, 628.
[43] Arrowsmith, M.; Hill, M. S.; Hadlington, T.; Kociok-Köhn, G.; Weetman, C. Organometallics 2011, 30, 5556.
[44] Mukherjee, D.; Ellern, A.; Sadow, A. D. Chem. Sci. 2014, 5, 959.
[45] Brown, H. C.; Schlesinger, H. I.; Burg, A. B. J. Am. Chem. Soc. 1939, 61, 673.
[46] De Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007.
[47] Oro, L. A.; Carmona, D.; Fraile, J. M. In Metal-Catalysis in Industrial Organic Processes, Eds.:Chiusoli, G. P.; Maitlis, P. M., RSC Publishing, London, 2006, 79.
[48] Weetman, C.; Anker, M. D.; Arrowsmith, M.; Hill, M. S.; Kociok-Köhn, G.; Liptrot, D. J.; Mahon, M. F. Chem. Sci. 2016, 7, 628.
[49] Chakrabarty, S.; Choudhary, S.; Doshi, A.; Liu, F.-Q.; Mohan, R.; Ravindra, M. P.; Shah, D.; Yang, X.; Fleming, F. F. Adv. Synth. Catal. 2014, 356, 2135.
[50] Weetman, C.; Hill, M. S.; Mahon, M. F. Chem. Commun. 2015, 51, 14477.
[51] Weetman, C.; Hill, M. S.; Mahon, M. F. Chem.-Eur. J. 2016, 22, 7158.
[52] Xu, D.-D.; Shan, C. H.; Bai, R. P.; Lan, Y. Chin. J. Org. Chem. 2017, 37, 190(in Chinese). (徐冬冬, 单春晖, 白若鹏, 蓝宇, 有机化学, 2017, 37, 190.)
[53] Berg, J. M.; Tymoczko, J. L.; Stryer, L. In Biochemistry, 5th ed., Ed.:Freeman, W. H., Philadelphia, PA, 2002.
[54] Schramm, M.; Thomas, G.; Towart, R.; Franckowiak, G. Nature 1983, 303, 535.
[55] Intemann, J.; Lutz, M.; Harder, S. Organometallics 2014, 33, 5722.
[56] Togni, G.; Grützmacher, H. Catalytic Heterofunctionalization, VCH, Weinheim, 2001.
[57] Delacroix, O.; Gaumout, A. C. Curr. Org. Chem. 2005, 9, 1851.
[58] Crimmin, M. R.; Barrett, A. G. M.; Hill, M. S.; Hitchcock, P. B.; Procopiou, P. A. Organometallics 2007, 26, 2953.
[59] Crimmin, M. R.; Barrett, A. G. M.; Hill, M. S.; Hitchcock, P. B.; Procopiou, P. A. Organometallics 2008, 27, 497.
[60] Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983.
[61] Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042.
[62] Liu, B.; Roisnel, T.; Åois Carpentier, J.-F.; Sarazin, Y. Angew. Chem., Int. Ed. 2012, 51, 4943.
[63] Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organosilicon Compounds, Vol. 2, Eds.:Rappoport, Z.; Apeloig, Y., Wiley, New York, 1998, p. 1687.
[64] Buch, F.; Brettar, J.; Harder, S. Angew. Chem., Int. Ed. 2006, 45, 2741.
[65] Bauer, H.; Alonso, M.; Färber, C.; Elsen, H.; Pahl, J.; Causero, A.; Ballmann, G.; De Proft, F.; Harder, S. Nat. Catal. 2018, 1, 40.

碱土金属促进氢官能团化反应的研究进展

Recent Advances in Alkaline-Earth-Metal-Catalyzed Hydrofunctionalization Reactions

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	贾小英, 普佳霞, 韩丽荣, 李清寒. 含双杂原子苯并[d]五元杂环硫醚类化合物的合成研究进展[J]. 有机化学, 2024, 44(1): 18-40.
[2]	赵茜帆, 陈永正, 张世明. 碳基非金属催化剂在有机合成领域的应用及机理研究[J]. 有机化学, 2024, 44(1): 137-147.
[3]	普佳霞, 贾小英, 韩丽荣, 李清寒. 可见光诱导C—N键断裂构建C—C键的研究进展[J]. 有机化学, 2023, 43(8): 2591-2613.
[4]	陆祖嘉, 秦涧, 吴金婷, 曹文丽, 匡保龙, 张建国. 1,2,3-三唑类含能化合物的合成研究进展[J]. 有机化学, 2023, 43(2): 526-554.
[5]	刘鹏, 钟富明, 廖礼豪, 谭伟强, 赵晓丹. 炔烃参与的去芳构化反应构建螺环己二烯酮类化合物的研究进展[J]. 有机化学, 2023, 43(12): 4019-4035.
[6]	雍灿, 李芸, 毕涛, 陈国凤, 郑东霞, 王周玉, 张园园. 基于D-半乳糖衍生的小分子半乳糖凝集素抑制剂的合成及活性研究进展[J]. 有机化学, 2022, 42(5): 1307-1325.
[7]	张志豪, 姜芯, 李清寒. 取代苯并[b]呋喃衍生物的合成研究进展[J]. 有机化学, 2022, 42(4): 945-964.
[8]	赵咪娜, 杨梓墨, 杨得锁. 通过环化反应构建多取代咪唑的最新研究进展[J]. 有机化学, 2022, 42(1): 111-128.
[9]	张雷, 杨晨, 郭雪峰, 莫凡洋. Suzuki-Miyaura偶联反应机理研究进展[J]. 有机化学, 2021, 41(9): 3492-3510.
[10]	季长兴, 王光霞, 王华. 基于亚组分自组装的金属有机超分子研究进展[J]. 有机化学, 2021, 41(6): 2261-2279.
[11]	徐学涛, 陈洁, 柯俊杰, 张焜, 吴盼盼, 王少华. 不同环化方式下吡咯合成的研究进展[J]. 有机化学, 2021, 41(1): 206-228.
[12]	刘玉婷, 李洁, 尹大伟. 基于二茂铁的金属阳离子识别受体的研究进展[J]. 有机化学, 2021, 41(1): 158-170.
[13]	贾乾发, 李娅琼, 林银河. 有机催化芳香化反应的研究进展[J]. 有机化学, 2020, 40(6): 1502-1513.
[14]	张艳霞, 韩建伟. 手性膦腈碱有机催化的研究进展[J]. 有机化学, 2020, 40(10): 3154-3165.
[15]	王少华, 张帮红, 陈洁, 郑莹莹, 冯娜, 马爱军, 徐学涛, Abdullah M. Asiri. 多取代吡唑合成最新研究进展[J]. 有机化学, 2020, 40(1): 15-27.