杨帆,男,硕士生导师,郑州大学青年骨干教师,
出生年月:1982年6月,最后学历:博士,职称:副教授
学习经历:
2004年郑州大学化学系基地班毕业,获理学学士学位(导师:吴养洁院士);
2009年郑州大学化学系毕业,获理学博士学位(导师:吴养洁院士)。
联系方式:
邮箱:yangf@zzu.edu.cn
研究方向:
- 炔烃衍生物为原料的有机合成方法学
取代炔烃和共轭炔烃体系作为一种重要的结构骨架在天然产物、药物化学中间体、医药、农药、光电材料和纳米分子器件的合成中发挥着极为关键的作用,其中,末端炔烃参与的Sonogashira反应是合成取代炔烃和大的共轭炔烃最为简便而有效的途径之一。不仅如此,取代炔烃上的叁键还很容易发生加成反应,如著名的Larock环化反应即是此类反应的典范,已成为合成吲哚、喹啉、吲哚酮、吡咯等各种氮杂环化合物的有效方法之一。由于炔烃同时兼具弱酸性和不饱和叁键的特点,使其所参与的反应具有类型多样、产物类别与结构丰富等特性,由此发展出新的合成反应与合成方法不断涌现。
2. 惰性化学键的断裂与官能化
C−H键和C−C键等作为常见的化学键,广泛存在于有机化学分子中。由于它们键能大、断裂困难,通常被认为是惰性键,长期得不到化学家的重视。其中,C−H键的官能化问题因难度很大,更被称为有机化学中的“圣杯”。当前,惰性键的官能化研究得益于现代有机化学的发展,已成为有机化学领域中最富有活力和创造力的前沿课题之一,过渡金属参与的惰性化学键的活化和官能化反应主要集中在C−H键和C−C键的反应上,该类反应一般采用过渡金属如Pd、Cu、Rh、Ru和Ir等作为催化剂。
3. 苯并杂环衍生物的简便合成
苯并芳杂环衍生物(如吲哚、苯并呋喃、喹啉等)是一类重要的有机合成中间体,芳杂环结构单元广泛存在于天然产物、药物、香料、染料、杀虫剂和生物大分子中,并且在某些药物和生物大分子中显示出生物活性和药理活性[1]。传统的合成方法通常是合成路线冗长、效率低的多步反应,且较多使用有毒试剂,如常用的Fischer吲哚类衍生物合成法存在产率低、区域选择性差和使用毒性较大的的苯肼类试剂等缺点。在过去的三十多年里,导向有机合成的金属有机化学(OMCOS)的快速发展改变了传统有机合成化学的面貌,这种金属参与现代有机合成反应不同于传统的多步合成反应,这因为它更符合高效、高选择性、环境友好和原子经济性等现代合成化学的要求,由此发展出的过渡金属参与的新有机合成方法已成为构建芳杂环结构单元最简便、高效的方法之一。
承担科研项目:
- 2012.1~2014.12,苯并杂环衍生物的新合成方法研究,国家自然科学基金资助课题,编号:21102134
部分代表性论文与专著:
[1] Xiang Li, Fan Yang*, Yangjie Wu, Yusheng Wu*, Copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water, Org. Lett. 2014, 16, 992−995.
[2] Kai Xu, Suyan Sun, Guodong Zhang, Fan Yang*, Yangjie Wu*, One-pot synthesis of unsymmetrical diarylacetylenes via Sonogashira/deacetonation/Sonogashira cross-coupling of two different aryl chlorides with 2-methyl-3-butyn-2-ol, RSC Adv. 2014, 4, 32643−32646.
[3] Qian Zhang, Fan Yang*, Yangjie Wu*, DDQ: the chlorinating reagent and oxidant for the ligand-directed ortho-chlorination of 2-arylpyridines, Org. Chem. Front. 2014, 1, 694−697.
[4] Xiang Li, Fan Yang*, Yangjie Wu*, Synthesis of diarylalkynes via tandem Sonogashira/decarboxylative reaction of aryl chlorides with propiolic acid, RSC Adv. 2014, 4, 13738−13741.
[5] Qian Zhang, Fan Yang*, Yangjie Wu*, Palladium-catalyzed ortho-acylation of 2-aryl pyridinederivatives using arylmethyl amines as new acyl sources, Chem. Commun. 2013, 49, 6837−6839. (Featured as Back Cover)
[6] Kai Xu, Fan Yang*, Guodong Zhang, Yangjie Wu*, Palladacycle-catalyzed phosphonation of aryl halide in water, Green Chem. 2013, 15, 1055−1060.
[7] Xiang Li, Fan Yang*, Yangjie Wu*, Palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides under air, J. Org. Chem. 2013, 78, 4543−45550.
[8] Hao Hu, Fan Yang*, Yangjie Wu*, Palladacycle-catalyzed deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides, J. Org. Chem. 2013, 78, 10506−10511.
[9] Kai Xu, Hao Hu, Fan Yang*, Yangjie Wu*, Synthesis of aryl and arylmethyl phosphonates by cross-coupling of aryl or arylmethyl halides (X = I, Br and Cl) with diisopropyl H-phosphonate, Eur. J. Org. Chem. 2013, 319−325.
[10] Qian Zhang, Fan Yang*, Yangjie Wu*, Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles using arylmethyl alcohols as the acyl source, Tetrahedron 2013, 69, 4908−4914.
[11] Qian Zhang, Chao Li, Fan Yang*, Jingya Li, Yangjie Wu*, Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles, Tetrahedron 2013, 69, 320−326.
[12] Ang Gao, Fan Yang*, Ji Li, Yangjie Wu*, Pd/Cu-catalyzed oxidation of alkynes into 1,2-diketones using DMSO as the oxidant, Tetrahedron 2012, 68, 4950−4954.
[13] Yuting Leng, Fan Yang*, Weiguo Zhu, Yangjie Wu*, Xiang Li, Chlorination and ortho-acetoxylation, Org. Biomol. Chem. 2011, 9, 5288−5296.
[14] Yuting Leng, Fan Yang*, Weiguo Zhu, Dapeng Zou, Yangjie Wu*, Ranran Cai, Facile synthesis of arylboronic esters by palladacycle-catalyzed bromination of 2-arylbenzoxazoles and subsequent borylation of the brominated products, Tetrahedron 2011, 67, 6191−9196.
[15] Fan Yang, Junli Zhang, Yangjie Wu*, Facile synthesis of isoquinolines by imination and subsequent palladacycle-catalyzed iminoannulation of internal alkynes, Tetrahedron 2011, 67, 2969−2973.
[16] Fan Yang, Yangjie Wu*, Yanan Li, Biao Wang, Junli Zhang, Modified palladium-catalyzed regioselective ortho-arylation of sp2 C–H bond substrates with a low catalyst loading, Tetrahedron 2009, 65, 914−919.
[17] Fan Yang, Yangjie Wu*, Zhiwu Zhu, Junli Zhang, Yanan Li, Direct ortho-arylation of 2-arylbenzoxazoles via C–H activation, Tetrahedron 2008, 64, 6782−6787.
[18] Fan Yang, Yangjie Wu*, Facile Synthesis of Substituted Alkynes by Cyclopalladated Ferrocenylimine Catalyzed Cross-Coupling of Arylboronic Acids/Esters with Terminal Alkynes, Eur. J. Org. Chem. 2007, 3476−3479.
[19] Fan Yang, Xiuling Cui, Yanan Li, Jinli Zhang, Gerui Ren, Yangjie Wu*, Cyclopalladated ferrocenylimines: efficient catalysts for homocoupling and Sonogashira reaction of terminal alkynes, Tetrahedron 2007, 63, 1963−1969.
[20] 杨帆, 崔秀灵*, 现代有机反应第六卷: 金属催化反应II(金属催化的氧化偶联反应), 化学工业出版社, 47.8万字, 2012.