课题组负责人:梁云,博士,教授,博士生导师
联系方式:yliang@hunnu.edu.cn
本课题组秉承“理想合成”的科学理念。致力于金属促进的碳碳键、碳氢键及碳杂原子键的切断和构建的研究。发现价键切断和构建的规律和机制,发展高效的、 选择性的和绿色的有机合成方法,实现有用物质的理想合成。
目前研究工作主要集中在下面三个方面:
1. 通过构建碳硫键合成有机含硫化合物;
2. 通过构建碳硅键合成有机硅化合物;
3. 发展过渡金属催化的交叉偶联-串联反应策略。
课题组主要科学研究基金项目:
1. 国家自然科学基金面上项目:基于二硅烷捕捉有机钯中间体的策略合成有机硅化合物(21971061);65万(在研)(2020-2023);项目负责人:梁云。
2. 国家自然科学基金面上项目:基于无机硫源的偶联-串联反应合成硫杂环化合物研究(21572051);65万(在研)(2016-2019);项目负责人:梁云。
3. 湖南省自然科学基金重点项目:基于过渡金属催化sp3碳硅键的活化合成噻咯的研究(18A002);6万(在研)(2019-2021);项目负责人:梁云。
4. 国家自然科学基金面上项目:基于芳炔与碘叶立德反应及其应用的研究(21072054);34万(结题)(2011-2013);项目负责人:梁云。
5. 教育部科学技术项目:基于芳炔与羧酸酯的反应及其在有机合成中应用研究(213027A);50万(结题)(2013-2016);项目负责人:梁云。
6. 教育部博士点新教师基金:基于邻三甲基硅芳基三氟磺酸酯为芳炔的前体与碘叶立德反应的研究(20094306120003),3.6万(结题)(2010-2012);项目负责人:梁云。
7. 湖南省自然科学基金重点项目:基于芳炔与羧酸酯的反应及其在有机合成中应用研究(12JJ2009);20万(结题)(2012-2015);项目负责人:梁云。
8. 湖南省教育厅科学技术重点项目:基于无机硫盐的双硫化反应合成硫醚和硫杂环化合物的研究(15A109);8万(结题)(2015-2018);项目负责人:梁云。
9. 湖南省教育厅科学技术重点项目:基于芳炔与羧酸酯的反应及其在有机合成中应用研究(12A095);8万(结题)(2012-2015);项目负责人:梁云。
10.湖南省普通高校青年骨干教师,2万(2012);项目负责人:梁云。
11.湖南师范大学优秀青年项目:基于芳炔与碘叶立德反应及其应用的研究 (ET21003);10万(结题)(2010-2012);项目负责人:梁云。
12.北京分子科学国家实验室开放基金:基于1,1-偕二卤-1,4-共轭二卤化合物多反应位点的交叉偶联-串联反应研究。5万(结题)(2012-2014);项目负责人:梁云。
课题组主要论文发表:
1. Yang, Y.; Zhou, L.; Yang, X.; Luo, X.; Deng, G.;Yang, Y.*;Liang, Y.* Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, ando-Bromobenzoic Acids, Synthesis 2020, 52, 1223-1230.
2. Luo, X.; Li, W.; Lu, H.; Deng, G.;Yang, Y.*; Yang, C.*;Liang, Y.* Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring, Chin. Chem. Lett. 2020, DOI: 10.1016/j.cclet.2020.07.005.
3. Li, W.; Zhang, C.; Lu, H.; Wang, Y.; Deng, G.;Liang, Y.*;Yang, Y.*Pd-Catalyzed one-pot synthesis of vinylsilanes via a three-component tandem reaction. Org. Chem. Front. 2020, 7, 2075-2081.
4. Lu, H.; Yang, X.; Zhou, L.; Li, W.; Deng, G.; Yang, Y.*;Liang, Y.* Palladium-catalyzed domino Heck-disilylation and -borylation of alkene-tethered 2-(2-halophenyl)-1H-indoles: access to diverse disilylated and borylated indolo[2,1-a]isoquinolines, Org. Chem. Front. 2020, 7, 2016-2021.
5. Xiaoming Zhu,* Fuxing Zhang, Daizhi Kuang, Guobo Deng, Yuan Yang, Jiangxi Yu,* andYun Liang*, K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2‑Unsubstituted Benzothiazoles, Org.Lett., 2020, 22, 3789-3793.
6. Xiaoming Zhu, Fengru Zhou, Yuan Yang, Guobo Deng,* andYun Liang*, Catalyst- and Additive-Free Method for the Synthesis of 2‑Substituted Benzothiazoles from Aromatic Amines, Aliphatic Amines, and Elemental Sulfur, ACS Omega 2020, 5, 13136-13147.
7. Wenqi Chen, Xiaoming Zhu, Fei Wang, Yuan Yang, Guobo Deng,* andYun Liang*, Iodine-Catalyzed Three-Component Cascade Reaction for the Synthesis of Substituted 2‑Phenylnaphtho[1,3]selenazoles under Transition-Metal-Free Conditions, J. Org. Chem., 2020, 85, 3349-3357.
8. Luo, X.; Zhou, L.; Lu, H.; Deng, G.;Liang, Y.*; Yang, C.*;Yang, Y.*Palladium-Catalyzed Domino Heck/C-H Activation/Decarboxylation: A Rapid Entry to Fused Isoquinolinediones and Isoquinolinones, Org. Lett. 2019,21, 9960.
9. Li, W.; Chen, W.; Zhou, B.; Xu, Y.; Deng, G.;Liang, Y.*; Yang, Y.*NBE-Controlled Palladium-Catalyzed Interannular Selective C−H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2- Acetamides, Org. Lett. 2019, 21, 2718.
10. Yang, X.; Lu, H.; Zhu, X.; Zhou, L.; Deng, G.; Yang, Y.*;Liang, Y.*Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with o‑Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1‑a]isoquinolines, Org. Lett. 2019, 21, 7284.
11. Chen, L.; Min, H.; Zeng, W.; Zhu, X.;Liang, Y.*; Deng, G.*; Yang, Y.*Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C−H Bonds, Org. Lett. 2018, 20, 7392.
12. Yang, Y.; Zhou, B.; Zhu, X.; Deng, G.;Liang, Y.*; Yang, Y.*Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C−H Activation and Decarboxylation, Org. Lett. 2018, 20, 5402.
13. Luo, X.; Xu, Y.; Xiao, G.; Liu, W.; Qian, C.; Deng, G.; Song, J.;Liang, Y.*; Yang, C.*Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C−H Activation, Org. Lett. 2018, 20, 2997.
14. Zhu, X.; Li, W.; Luo, X.; Deng, G.;Liang, Y.*; Liu, J.*A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from o-iodoanilines, DMSO and potassium sulfide, Green Chem. 2018, 20, 1970.
15. Xiao, G.; Chen, L.; Zhou, B.; Deng, G.; Gong, J.;Liang, Y.*Palladium-Catalyzed Domino Heck/Silylation Reaction for the Synthesis of (2-Oxoindolin-3-yl)methylsilanes via Trapping of the s-Alkylpalladium Intermediates with Disilanes, Adv. Synth. Catal. 2018, 360, 3477.
16. Li, W.; Xiao, G.; Deng, G.;Liang, Y.*Pd-Catalyzed disilylation: an efficient route to 2,2’-bis(trimethylsilyl)biphenyls via trapping transient dibenzopalladacyclopentadienes with hexamethyldisilane, Org. Chem. Front. 2018, 5, 1488.
17. Xu, Y.; Liu, X.; Chen, W.; Deng, G.;Liang, Y.*; Yang, Y.*Palladium/Norbornene Chemistry: Synthesis of Norbornene-Containing Arylsilanes Involving Double C−Si Bond Formation, J. Org. Chem. 2018, 83, 13930.
18. Zheng, Z.; Chen, L.; Qian, C.; Zhu, X.; Yang, X.; Liu, J.*; Yang, Y.*;Liang, Y.*Copper-catalyzed synthesis of 2-acylbenzo[b]thiophenes from 3-(2-iodophenyl)-1-arylpropan-1-ones and potassium sulfide under aerobic conditions, Org. Biomol. Chem. 2018, 16, 8020.
19. Zhou, B.; Chen, W.; Yang, Y.; Yang, Y.; Deng, G.*;Liang, Y.*A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates, Org. Biomol. Chem. 2018, 16, 7959.
20. Xiao, G.; Min, H.; Zheng, Z.; Deng, G.*;Liang, Y.*Copper-catalyzed three-component reaction of imidazo[1,2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1,2-a]pyridines, Chin. Chem. Lett. 2018, 29, 1363.
21. Xiao, G.; Chen, L.; Deng, G.; Liu, J.*;Liang, Y.*Disilylation of N-(2-Halophenyl)-2-phenylacrylamides with hexamethyldisilane via trapping the spirocyclic palladacycles, Tetrahedron Lett. 2018, 58, 1836.
22. Liu, X.; Deng, G.*;Liang, Y.*Selective synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines via coppercatalyzed tandem annulation of alkynylbenzonitriles with 2-Iodoanilines, Tetrahedron Lett. 2018, 58, 2844.
23. Liu, W.; Min, H.; Zhu, X.; Deng, G.*;Liang, Y.*Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide, Org. Biomol. Chem., 2017, 15, 9804.
24.Zhu, X.; Yang, Y.; Xiao, G.; Song, J.;Liang, Y.*; Deng, G.* Double C-S bond formation via C-H bond functionalization: synthesis of benzothiazoles and naphtho[2,1-d]thiazoles from N-substituted arylamines and elemental sulfur, Chem. Comm. 2017, 53, 11917.
25.Dang, P.; Zheng, Z.;Liang, Y.*Copper-Catalyzed C(sp3)−S Bond and C(sp2)−S Bond Cross-Coupling of 2‑(2-Iodobenzoyl) Substituted or 2‑(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds, J. Org. Chem. 2017, 82, 2263.
26. Wu, L.; Deng, G.*;Liang, Y.* Synthesis of dibenzo[a,c]carbazoles from 2-(2-halophenyl)-indoles and iodobenzenes via palladium-catalyzed dual C–H functionalization, Org. Biomol. Chem., 2017, 15, 6808.
27.Zhou, S.; Xia, G.;Liang, Y.*Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides, Tetrahedron, Lett. 2017, 58, 338.
28. Huang, H.; Dang, P.; Wu, L.;Liang, Y.*; Liu, J.*Copper-catalyzed synthesis of benzo[b]thiophene-fused imidazopyridines via the cleavage of C–H bond and C–X bond, Tetrahedron Lett. 2016, 57, 574.
29. Zheng, Z.; Deng, G.;*Liang, Y.*Synthesis of quinolines through copper-catalyzed intermolecular cyclization reaction from anilines and terminal acetylene esters, RSC Adv. 2016, 6, 103478.
30. Min, H.; Xiao, G.; Liu, W.;Liang, Y.*Copper-catalyzed synthesis of 2-aminobenzothiazoles from 2-iodophenyl isocyanides, potassium sulfide and amines, Org. Biomol. Chem., 2016, 14, 11088.
31.Dang, P.; Zeng, W.;Liang, Y.*Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o‑Iodoanilines, Isocyanide, and Potassium Sulfide, Org. Lett. 2015, 17, 34.
32. Wu, L.; Huang, H.; Dang, P.;Liang, Y.*; Pi, S. Construction of benzo[a]carbazole derivatives via Diels–Alder reaction of arynes with vinylindoles, RSC Adv. 2015, 5, 64354.
33. Yang, Y.; Huang, H.; Liu, W.;Liang, Y.*Dual Role of Alkynyl Bromides in One-Step Synthesis of Bromo-Substituted Alkynyl Sulfides, Synthetic Communications 2015, 45, 86.
34. Zhang, X.; Zeng, W.; Yang, Y.; Huang, H.;Liang, Y.*Copper-Catalyzed Double C−S Bonds Formation via Different Paths: Synthesis of Benzothiazoles from N‑Benzyl-2-iodoaniline and Potassium Sulfide, Org. Lett. 2014, 16, 876.
35. Wu, L.; Huang, H.;Liang, Y.*; Cheng, Pi. Regio- and Stereoselective Synthesis of 2‑Amino-dienes via Decarboxylative Amination of 4‑(Ethoxycarbonyl)-2,3-allenols by TsNCO, J. Org. Chem. 2014, 79, 11264.
36. Yang,Y.; Huang, H.; Wu, L.;Liang, Y.* Palladium-catalyzed annulation of benzynes with N-substituted-N-(2-halophenyl)formamides: synthesis of phenanthridinones, Org. Biomol. Chem. 2014, 12, 5351.
37.Yang, Y.; Zhang, X.; Zeng, W.; Huang, H.;Liang, Y.*Copper catalyzed three-component synthesis of benzothiazolones fromo-iodoanilines, DMF, and potassium sulfide, RSC Adv. 2014, 4, 6090.
38.Zeng, W.; Dang, P.; Zhang, X.;Liang, Y.*; Peng, C.Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide, RSCAdv. 2014, 4, 31003.
39. Huang, H.; Yang, Y.; Zhang, X.; Zeng, W.Liang, Y.*,Transition-metal-free approach to synthesis of indolines from N-(ortho-chloromethyl)aryl amides and iodoniumylides, Tetrahedron Lett. 2013, 54, 6049.
40. Yang, Y.; Huang, H.; Zhang, X.; Zeng, W.;Liang, Y.*,Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides, Synthesis 2013, 3137.
41. Zhang, X.; Zeng, W.; Yang, Y.; Huang, H.;Liang, Y.*,Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes fromo-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process, Synlett. 2013, 24, 1687.
42.Liang, Y.; Geng, W.; Wei, J.; Xi, Z.*Palladium-Catalyzed Intermolecular Coupling of 2-Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene-Fused Siloles by Catalytic Cleavage of the C(sp3)-Si Bond, Angew. Chem. Int. Ed. 2012, 51, 1934.
43.Liang, Y.; Geng, W.; Wei, J.; Ouyang, K.; Xi, Z.*Palladium-catalyzed SilylC(sp3)-H Bond Activation, Org. Biomol. Chem. 2012, 10, 1537.
44. Yang, Y.; Zhang, X.;Liang, Y.* Copper-catalyzed coupling of 1,2-dibromo-1-styrenes with sulfonamidesfor the preparation of ynamides, Tetrahedron Lett. 2012, 53, 6557.
45. Zhang, X.; Yang, Y.;Liang, Y.* Palladium-catalyzed double N-arylation to synthesize multisubstituteddibenzoazepine derivatives, Tetrahedron Lett. 2012, 53, 6406.
46. Liang, Y.; Zhang, S, Xi, Z.* Palladium-Catalyzed Synthesis of Benzosilolo[2,3-b]indoles via Cleavage of a C(sp3)-Si Bond and Consequent Intramolecular C(sp2)-Si Coupling,J. Am. Chem. Soc.2011,133, 9204.
47. Liang,Y.;Meng, T.; Zhang, H.; Xi, Z.* Palladium-catalyzed, one-pot, three-component approach toa-alkynylindoles fromo-bromo-(2,2-dibromovinyl)benzenes, terminal alkynes and arylamines, Synlett. 2011, 911.
48. Pi, S.-F.; Yang, X.-H.; Huang, X.-C.;Liang, Y.*; Yang, G.-N.; Zhang, X.-H.; Li, J.-H.* Palladium-Catalyzed Cyclocarbonylation of Arynes with Methyl Allyl Carbonates: Selective Synthesis of 1H-Inden-1-ones, J. Org. Chem. 2010, 75, 3484.
49. Li, R.-J.; Pi, S.-F.;Liang, Y.*; Wang, Z.-Q.; Song, R.-J.; Chen, G.-X.; Li, J.-H.* Palladium-catalyzed annulations of arynes with 2-(2-iodophenoxy)-1-substituted ethanones, Chem. Commun. 2010, 8183.
50. Liu, Y.-L.;Liang, Y.*; Pi, S.-F.; Li, J.-H.*,Selective Synthesis ofo-Acylbenzylphosphonates by Insertion Reactions of Arynes into β-Ketophosphonates, J. Org. Chem. 2009, 74, 5691.
51. Pi, S.-F.; Tang, B.-X.; Li, J.-H.*; Liu, Y.-L.;Liang, Y.*, Palladium-Catalyzed Decarboxylative Coupling of Allylic Alkynoates with Arynes, Org. Lett. 2009, 11, 2309.
52. Liu, Y.-L.;Liang, Y.*; Pi, S.-F.; Huang, X.-C.; Li, J.-H.*, Palladium-Catalyzed Cocyclotrimerization of Allenes with Arynes: Selective Synthesis of Phenanthrenes, J. Org. Chem. 2009, 74, 3199.
53. Huang, X.-C.; Wang, F.;Liang, Y.*; Li, J.-H.*, Halopalladation/Decarboxylation/ Carbon-Carbon Forming Domino Process: Synthesis of 5-Halo-6-substituted Benzo[b]naphtho[2,1-d]furans, Org. Lett. 2009, 11, 1139.
54. Huang, X.-C.; Liu, Y.-L.;Liang, Y.*; Pi, S.-F.; Wang, F.; Li, J.-H.*, Cycloaddition of Arynes with Iodonium Ylides: A Mild and General Route for the Synthesis of Benzofuran Derivatives, Org. Lett. 2008, 10, 1525.
55. Xie, Y.-X.; Wang, J.; Li, J.-H.*;Liang, Y.*, Reusable and Ligand-Free Palladium-Catalyzed Suzuki-Miyaura Cross-Couplings of Aryl Halides with Arylboronic Acids in Tetra-n-butylammonium Bromide, Chin. J. Chem. 2008, 26, 2261.
56.Liang, Y.;Tao, L.-M.; Zhang, Y.-H.; Li, J.-H.*, Palladium-Catalyzed Cross-Coupling Reactions of 1,2-Diiodoalkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1,3-diynes and 2-Ethynylbenzofurans, Synthesis 2008, 3988.