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熊燕
2017-04-12 20:29   审核人:

熊燕 教授,博士生导师,1975年生。2007年毕业于四川大学有机化学专业,获博士学位,师从中科院院士冯小明教授,从事不对称催化合成研究。2008年爱尔兰都柏林大学CSCB研究中心做博士后,从事超价碘化学与过渡金属催化去对称化研究,爱尔兰政府IRCSET学者,导师Dr. Hasim Ibrahim 2009年回国,重庆大学任教,从事有机化学的教学科研工作。2014年北京大学做访问学者,导师中科院院士刘忠范教授,主要从事新型骨架构建的碳材料研究。

学术研究成果:(1基于超价碘氧化,发展了极性反转的Umpolung碳杂键不对称形成反应、富电子位点的Umpolung氰化反应、酮亚胺的氧化重排反应,实现了多样性噁唑、咪唑杂环的构建,合成了氯苄达唑(Chlormidazole)、克立咪唑(Clemizole)药物;(2)基于BF3-H2O超酸体系和碳正离子中间体,利用苄醇、苄氯、苄醚发展了芳烃的苄基化反应、交叉醚化反应及其绿色合成过程,合成了降血脂药物苄氯贝特(Beclobrate);(3)基于氧化的单电子转移的自由基过程,高选择性地实现了苯胺的4,4‘-氧化偶联构建系列联芳胺、偶联氰化得到系列α-氨基腈、偶联亚磷酸酯化得到系列α-氨基磷酸酯等。相关工作发表在Adv. Mater.Chem. Eur. J.Green Chem.Chem. Commun., Org.Lett.Org. Chem. Front. J. Org. Chem.Adv. Synth. Catal.TetrahedronTetrahedron Lett.Org. Biomol. Chem.SynlettSynthesisRSC Advances等有机化学主流刊物上,总引次数683次,最高单篇他引158次。发明专利获授权6项。

主要教学成果:主持重庆市高等学校教学改革重点项目1项,深入探讨了以实验竞赛推动实验室开放的课题,相关成果获重庆大学教学成果二等奖(2017)、重庆市优秀硕士论文奖指导教师(2016)、重庆大学优秀硕士论文指导教师(2015), 三届卓越联盟卓越杯大学生化学新实验设计一等奖指导教师(201420152017),国家大学生创新实验优秀奖指导教师(2017)。

研究方向:

1. 化学工程与技术。化工新材料,新型骨架碳材料的设计、制备和表征;有机化工工艺路线的设计与开发。

2. 有机化学。不对称合成,从事具有生物活性的手性农药、医药及其中间体的合成。

主讲课程:本科生《有机化学》

联系方式: Emailxiong@cqu.edu.cn

Dr. Yan Xiong was born in Sichuan in 1975. In 2007, he obtained his Ph.D. degree having thesis entitled on the amine-mediated asymmetric synthesis supervised by the CAS academician Prof. Dr. Xiaoming Feng. After a postdoctoral appointment at UCD, Ireland, (Dr. Hasim Ibrahim), Yan joined Chongqing Unversity firstly as a Lecturer (2009), then promoted as an associate professor (2011) and awarded as professor title in organic chemistry (2016). In collaboration with CAS academician Prof. Zhongfan Liu working on the synthesis of graphdiyne, he visited Peking University in 2014. His research interest focuses on oxidative asymmetric synthesis and the synthesis of novel carbon materials. The members of his lab are postdocs, PhD students, master students and project undergraduates.

Xiong’s lab has a long-time collaboration with CNRS (France) as well and some academic activities are funded by international grants.

 

近期负责的科研项目:

[1] 国家自然科学基金面上项目(No. 21372265):手性甜菜碱类双功能基催化剂的设计合成及其在不对称亲电氰化反应中的应用研究,主持人,时间:2014.1-2017.12.

[2] 国家自然科学基金专项基金国际合作项目(No. 21350110501):Organocatalysis: a Green Technology to Convert Simple Feed-Stocks into Molecular Architectures of Biological Interest,主持人,时间:2014.1-2014.12.

[3] 重庆市“121”科技支撑示范工程:重庆化工新材料产业示范工程协同管理创新与应用研究/共性技术攻关,主持人,时间:2013.7-2016.12.

[4] 元素有机化学国家重点实验室(南开大学)开放基金(No. 201508):α/β-胺基腈合成与串联氰化反应研究,主持人,时间:2015.10-2016.10.

[5] 中法国际合作交流项目(PHC XU GUANGQI 2012No. 27967RE): L’Organocatalyse : une Technologie Verte pour la Valorisation des Phénols en Briques Moléculaires d’Intérêt Thérapeutique,主持人,时间:2012-2013.

[6] 企业合作项目.

近几年代表性成果:

一、授权专利:

[1] 熊燕,马航,黄若峰,张晓慧,潘静,李加强,凌学戈,何超,一种亚胺酸酯衍生物的合成方法,专利号:ZL201410157666.8.

[2] 熊燕,张晓慧,黄若峰,文森特·卡依福德(Vincent Coeffard),李昱,潘静,李加强,凌学戈,何超,一种苯并噁唑衍生物的合成方法,专利号:ZL201310756794.X.

[3] 黎学明,李昱,熊燕,杨建春,凌学戈,张晓慧,黄若峰,一种以苄醚为原料的二苯甲烷衍生物的合成方法,专利号:ZL201310652302.2

[4] 熊燕,张舒婷,张旭,凌学戈 一种芳烃的烯丙基化方法,专利号ZL201010560525.2.

[5] 熊燕,秦莉晓,张学强,凌学戈,周明,李赛 一种苯胺衍生物氧化偶联一步合成联苯二胺衍生物的方法,专利号ZL201010181689.4.

[6] 熊燕,张学强,周明,凌学戈,秦莉晓 一种醋酸乙酯与醇酯交换一步合成醋酸醇酯的方法,专利号:ZL201010172133.9.

二、代表性论文:

[1] Hang Shen, Qingfu Deng, Ruojuan Liu, Yangyang Feng, Yan Xiong* Hypervalent Iodine-Promoted Annulative Aminocyanation of Unactivated Alkenes. Org. Chem. Front. 2017, 4, 1806-1811. (IF = 5.0)

[2] Congke Zheng, Xiaohui Zhang, Muhammad Ijaz Hussain, Mingming Huang, Qing Liu, Yan Xiong,* Xiangming Zhu,* One-pot Dichlorinative Deamidation of Primary β-Ketoamides. Tetrahedron Lett. 2017, 58, 574-577.

[3] Jiaqiang Li, Ziqian Xie, Yan Xiong, Zhenzhu Li, Qunxing Huang, Shuqing Zhang, Jingyuan Zhou, Rong Liu, Xin Gao, Changguo Chen, Lianming Tong*, Jin Zhang*, Zhongfan Liu,* Architecture of β-Graphdiyne Contained Thin Film Using Modified Glaser-Hay Coupling Reaction for Enhanced Photocatalytic Property of TiO2. Adv. Mater. 2017, 29, 1700421. (IF = 19.8)

[4] Liangzhen Hu, Jing Pan, Xiaohui Zhang, Wen Hu, Yan Xiong,* Xiangming Zhu, Synthesis of N, O π-Conjugated Boron Complexes and the Reactivity of Suzuki Cross-Coupling. Tetrahedron 2017, 73, 223-229.

[5] Qing Liu, Xiaohui Zhang,* Yang He, Muhammad Ijaz Hussain, Wen Hu, Yan Xiong,* Xiangming Zhu, Oxidative Rearrangement Strategy for Synthesis of 2, 4, 5-Trisubstituted Oxazoles Utilizing Hypervalent Iodine Reagent. Tetrahedron 2016, 72, 5749-5753.

[6] Yangyang Feng, Ruofeng Huang, Liangzhen Hu, Vincent Coeffard,* Yan Xiong,* Enantioselective α-Oxytosylation of 1,3-Dicarbonyl Compounds Catalyzed by Chiral C2-Symmetric Iodoarenes. Synthesis 2016, 48, 2637-2644.

[7] Mingming Huang, Liangzhen Hu, Hang Shen, Qing Liu, Muhammad Ijaz Hussain, Jing Pan, Yan Xiong,* Metal-Free Strategy for Sulfination of Alcohols with Sodium Sulfinates: An Unexpected Access. Green Chem. 2016, 18, 1874-1879. (IF = 9.2)

[8] Hang Shen,  Liangzhen Hu, Qing Liu, Muhammad Ijaz Hussain, Jing Pan,  Mingming Huang, Yan Xiong,*  Iron-Catalysed Sequential Reaction towards alpha-Aminonitriles from Secondary Amines, Primary Alcohols and Trimethylsilyl Cyanide. Chem. Commun. 2016, 52, 2776-2779. (IF = 6.3)

[9] Yang Li, Ping Deng, Youmao Zeng, Yan Xiong, Hui Zhou,*  anti-Selective Asymmetric Henry Reaction Catalyzed by a Heterobimetallic Cu–Sm–Aminophenol Sulfonamide Complex. Org. Lett. 2016, 18, 1578-1581. (IF = 6.6)

[10] Youmao Zeng, Ping Deng, Shixiong Zhang, Hong Yan, Guojuan Liang, Yan Xiong, Hui Zhou,* An Ni–PyBisulidine Complex for the Asymmetric Hydrophosphonylation of Aldehydes. Org. Biomol. Chem. 2016, 14, 9221-9224.

[11] Hang Shen, Xiaohui Zhang, Qing Liu, Jing Pan, Wen Hu, Yan Xiong,* Xiangming Zhu, Direct Oxidative Cyanation of Tertiary Amines Promoted by in situ Generated Hypervalent Iodine(III)-CN Intermediate. Tetrahedron Lett. 2015, 56, 5628-5631.

[12] Jiaqiang Li, Hang Shen, Qing Liu, Mingming Huang, Congke Zheng, Jing Pan, Yan Xiong,* Changguo Chen,* BF3·OEt2-catalyzed Etherification of Alcohols: a Metal-free Pathway to Diphenylmethyl Ethers. Adv. Synth. Catal. 2015, 357, 3115-3120. (IF = 5.6)

[13] Hang Shen, Jiaqiang Li, Qing Liu, Jing Pan, Ruofeng Huang, Yan Xiong,* Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers. J. Org. Chem. 2015, 80, 7212-7218. (IF = 4.8)

[14] Jiaqiang Li, Qing Liu, Hang Shen, Ruofeng Huang, Xiaohui Zhang Yan Xiong,* Changguo Chen,* Ethers as Hydrogen Sources in BF3·OEt2 Promoted Reduction of Diphenylmethyl Alcohols, Ethers and Esters to Hydrocarbons. RSC Adv. 2015, 4, 85291-85295.

[15] Jing Pan, Jiaqiang Li, Ruofeng Huang, Xiaohui Zhang, Hang Shen, Yan Xiong,* Xiangming Zhu, Extension Studies on Iron(III)-Promoted Free Radical Oxidation of Anilines. Tetrahedron 2015, 71, 5341-5346.

[16] Jing Pan, Jiaqiang Li, Ruofeng Huang, Xiaohui Zhang, Hang Shen, Xuege Ling, Yan Xiong,* Xiangming Zhu, Direct Metal-Free N-Benzylaiton of Sulfonamides with Benzyl alcohols Promoted by Employing BF3·Et2O. Synthesis 2015, 47, 1101-1108.

[17] Xiaohui Zhang, Ruofeng Huang, Jérôme Marrot, Vincent Coeffard,* Yan Xiong,* Hypervalent Iodine-Mediated Synthesis of Benzoxazoles and Benzimidazoles via an Oxidative Rearrangement. Tetrahedron 2015, 71, 700-708.

[18] Ruofeng Huang, Xuege Ling, Xiaohui Zhang, Jing Pan, Chao He, Yan Xiong,* Benzylation of Arenes with Benzyl Halides Synergistically Promoted by in situ Generated Superacid Boron Trifluoride Monohydrate and Tetrahaloboric Acid. Tetrahedron 2015, 71, 1540-1546.

[19] Hang Ma, Yang He, Ruofeng Huang, Xiaohui Zhang, Jing Pan, Jiaqiang Li,  Chao He, Xuege Ling, Xuanlun Wang, Yan Xiong,*  Nucleophilic Imidoesterification of Dicarbonyl Compounds with Cyanatobenzenes through C-C Bond Formation. Chin. Chem. Lett. 2014, 25, 1327-1330.

[20] Shuting Zhang, Xiaohui Zhang, Xuege Ling, Chao He, Ruofeng Huang, Jing Pan, Jiaqiang Li, Yan Xiong,* Superacid BF3-H2O Promoted Benzylation of Arenes with Benzyl Alcohols and Acetates Initiated by Trace Water. RSC Adv. 2014, 4, 30768-30774.

[21] Yajun Liu, Ping Deng, Xiangyang Li, Yan Xiong, Hui Zhou,* Asymmetric Henry Reaction Catalyzed by a Chiral Dinuclear Nickel Complex. Synlett 2014, 25, 1735-1738.

[22] Chao He, Xiaohui Zhang, Ruofeng Huang, Jing Pan, Jiaqiang Li, Xuege Ling, Yan Xiong,* Xiangming Zhu, Synthesis of Structurally Diverse Diarylketones through the Diarylmethyl sp3 C-H Oxidation. Tetrahedron Lett. 2014, 55, 4458-4462.

[23] Yu Li, Yan Xiong,* Xueming Li,* Xuege Ling, Ruofeng Huang, Xiaohui Zhang, Jianchun Yang, Benzylation of Arenes with Benzyl Ethers Promoted by in situ Prepared Superacid BF3-H2O. Green Chem. 2014, 16, 2976-2981. (IF = 9.2)

[24] Zhiyong Wang*, Xiaoxiao Xing, Liun Xue, Yan Xiong, Ling Fang*. Iron(III) Chloride Catalyzed Formation of Aryl Hydrazides from Electron-Rich Arenes and Azodicarboxylates, Synthesis 2014, 757-760.

[25] Xiafei Xu, Yan Xiong,* Xuege Ling, Ximi Xie, Jie Yuan, Shuting Zhang, Zhongrong Song,* A Practical Synthesis of Bis(indolyl)methanes Catalyzed by BF3·OEt2. Chin. Chem. Lett. 2014, 25, 406-410.

[26] Xuege Ling, Yan Xiong,* Ruofeng Huang, Xiaohui Zhang, Shuting Zhang, Changguo Chen,* Synthesis of Benzidine Derivatives via FeCl3·6H2O-Promoted Oxidative Coupling of Anilines. J. Org. Chem. 2013, 78, 5218-5226. (IF = 4.8)

[27] Ramulu Akula, Yan Xiong, Hasim Ibrahim,* Electrophilic α-Cyanation of 1,3-Dicarbonyl Compounds. RSC Adv. 2013, 3, 10731-10735.

[28] Xue-Ge Ling, Yan Xiong,* Shu-Ting Zhang, Ruo-Feng Huang, Xiao-Hui Zhang, Effective Synthesis of Benzyl Halides Triggered by in situ Prepared Hypervalent Halides. Chin. Chem. Lett. 2013, 24, 45-48.

[29] Qixiang Guo,* Wei Wen, Lina Fu, Shunen Zhang, Lanxi Zhang, Yuwan Liu, Biao Xu, Yan Xiong, Organocatalytic Aldol Reaction of Indole-3-Carbaldehydes with Ketones: Synthesis of Chiral 3-Substituted Indoles. Tetrahedron Lett. 2013, 54, 4653-4654.

[30] Yan Xiong,* Shuting zhang, Xuege Ling, Xu Zhang, Jinyue Wang, Theoretical Investigation on Identical Anionic Halide-Exchange SN2 Reaction Processes on N-Haloammonium Cation NH3X+ (X = F, Cl, Br, and I). Int. J. Quantum Chem. 2012, 112, 2475-2481.

[31] Xu Zhang, Yan Xiong,* Shuting Zhang,Xuege Ling, Jinyue Wang, Changguo Chen,* Aldol Condensations of Aldehydes and Ketones Catalyzed by Primary Amine on Water. Asian J. Chem. 2012, 24, 751-755.

[32]  Yan Xiong,* Xueqiang Zhang, Significant Heterogeneous Carbonate Salt Catalyzed Acetylation of Alcohols via a Transesterification Process with Carbonate Salt-Activated Alcohol 1H NMR Evidence. Chin. J. Chem. 2011, 29, 1143-1148.

[33]  Shiyuan Zheng, Yan Xiong,* Jinyue Wang, Theoretical Studies on Identity SN2 Reactions of Lithium Halide and Methyl Halide: A Microhydration Model. J. Mol. Model. 2010, 16, 1931-1937.

[34]  Fei Wang, Xiaohua Liu, Xin Cui, Yan Xiong, Xin Zhou, Xiaoming Feng,* Asymmetric Hydrophosphonylation of α-Ketoesters Catalyzed by Cinchona-derived Thiourea Organocatalyst. Chem. Eur. J. 2009, 15, 589-592.

[35]  Shiyuan Zheng, Jinyue Wang and Yan Xiong,* Theoretical Investigation on Isomerization of Et2AlCN to Et2AlNC and Cyanation of Aldimine. J. Mol. Struct.: THEOCHEM 2008, 869, 83-88.

[36]  Yan Xiong, Fei Wang, Shunxi Dong, Xiaohua Liu, Xiaoming Feng,* Asymmetric Bisprolinamide-Catalyzed Cross-Aldol of Aldehydes. Synlett 2008, 73-75.

[37]  Yan Xiong, Yuehong Wen, Fei Wang, Bo Gao, Xiao Huang, Xiaohua Liu, Xiaoming Feng,* A Chiral Functionalized Salt-Catalyzed Asymmetric Michael Addition of Ketones to Nitroolefins. Adv. Synth. Catal. 2007, 349, 2156-2166.

[38] Yan Xiong, Fei Wang, Xiao Huang, Yuehong Wen, Xiaoming Feng,* A New Copper(I)-Tetrahydrosalen-Catalyzed Asymmetric Henry Reaction and Its Extension to Synthesis of (S)-Norphenylephrine. Chem. Eur. J. 2007, 13, 829-833.

[39]  Yuehong Wen, Yan Xiong, Lu Chang, Jinglun Huang, Xiaohua Liu, Xiaoming Feng,* Chiral Bisformamide as an Effective Asymmetric Organocatalyst for One-Pot Three-Component Strecker Reaction. J. Org. Chem. 2007, 72, 7715-7719.

[40] Fei Wang, Yan Xiong, Xiaohua Liu, Xiaoming Feng,* Asymmetric Direct Aldol Reaction of α-Keto Esters and Acetone Catalyzed by Organocatalyst. Adv. Synth. Catal. 2007, 349, 2665-2668.

[41] Yi Ren,* Jinggang Gai, Yan Xiong, Kuo-Hsing Lee, San-Yan Chu, Theoretical Study on the Identity Ion Pair SN2 Reactions of LiX with CH3SX (X = Cl, Br, and I): Structure, Mechanism, and Potential Energy Surface. J. Phys. Chem. A 2007, 111, 6615-6621.

[42]  Yan Xiong, Xiao Huang, Shaohua Gou, Jinglun Huang, Yuehong Wen, Xiaoming Feng,* Enantioselective Cyanosilylation of Ketones Catalyzed by a Nitrogen-Containing Bifunctional Catalyst. Adv. Synth. Catal. 2006, 348, 538-544.

[43] Shaohua Gou, Xiaohong Chen, Yan Xiong, Xiaoming Feng,* Highly Enantioselective Cyanation of Aldehydes Catalyzed by A Multicomponent Titanium Complex. J. Org. Chem. 2006, 71, 5732-5736.

[44] Yuehong Wen, Xiao Huang, Jinglun Huang, Yan Xiong, Bo Qin, Xiaoming Feng,* Asymmetric Cyanosilylation of Aldehydes Catalyzed by Novel Organocatalysts. Synlett 2005, 16, 2445-2448.

[45] Yan Xiong, Hua-jie Zhu, Yi Ren,* A Theoretical Study of The Gas-phase Ion Pair SN2 Reactions of Lithium Halide and Methyl Halide with Inversion and Retention Mechanisms. J. Mol. Struct.: THEOCHEM 2003, 664-665, 279–289.

科研条件:

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