基本信息:
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:有机硅杂环化合物合成导向的硅醚试剂设计及反应性研究(22371070);(2024-2027);
2.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);(2020-2023);
3.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);(2016-2019)
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);(2011-2013)
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);(2013-2016)
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),(2010-2012)
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);(2012-2015)
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);(2015-2018)
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);(2012-2015)
10.湖南省普通高校青年骨干教师,(2012)
11.奥门银河误乐城优秀青年项目:基于芳炔与碘叶立德反应及其应用的研究(ET21003);(2010-2012)
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。(2012-2014)
获奖:
1.“过渡金属钯、铜催化构建C-C键和C-N键方法的研究”湖南省2009年自然科学奖二等奖
2.第五届湖南省基础教育教学成果奖特等奖(2022)
3.2020年奥门银河误乐城优秀研究生导师
课题组主要论文发表:
1.Liwei Zhou*, Pengyang Jing, Zhiwei Li, Rui Liu, Jiannan Chen, Guobo Deng,Yun Liang*andYuan Yang*,Norbornene Derivatives-Controlled Palladium-Catalyzed Divergent Synthesis of Dibenzo[a,c]cycloheptenones and Fluorenones from Aryl Iodides and α-Oxocarboxylic Acids,Organic Lett.,2024,26,676.
2.Yan Chen, Ling Zhu, Xuliang Tan, Xiahong Chen, Guobo Deng,Yun Liang* and Yuan Yanga,*Pd(II)-Catalyzed C-H Silylation ofo-Alkynylanilines Initiated byan Aminopalladation To Access Disilylated 2-Phenyl-1H-indoles,Adv. Synth. Catal.2024,366, 183.
3.Yankun Xu, Mingjie Sun, Weiwei Xu, Guobo Deng,Yun Liang*, and Yuan Yang*,Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C–H Activation,J. Am. Chem.Soc.,2023, 145, 15303.
4.Shujia Qiao, Wenbo Deng, Guobo Deng,Yun Liang*and Yuan Yang*, Research advances in palladium-catalysed intermolecular C–H annulation of aryl halides with various aromatic ring precursors,Org. Biomol. Chem.,2022,20, 6275.
5.Fengru Zhou, Liwei Zhou, Pengyang Jing, Mingjie Sun, Guobo Deng,Yun Liang*and Yuan Yang*, Chemoselective Transformations of Cyclicβ‑Bromoacrylic Acids with Palladacycles Formed by Aryl Iodides to Access Fused or Spiro Polycycles,Org. Lett.,2022,24, 1400.
6.Xiahong Chen, Sen Lei, Yan Chen, Wenbo Deng, Guobo Deng,*Yun Liang*and Yuan Yang*,Decarboxylative cyclization of o-chlorobenzoic acids with C,C-palladacycles formed by an aminopalladation/dealkylation strategy to access dibenzo[a,c]carbazoles,Org. Chem. Front.,2022,9, 3414.
7.Yankun Xu, Weiwei Xu, Xinyang Chen, Xiai Luo, Haiyan Lu, Minghao Zhang, Xiumei Yang, Guobo Deng,Yun Liang*and Yuan Yang*,Me3SiSiMe2(OnBu): a disilane reagent for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement,Chem. Sci.,2021,12, 11756.
8.Liwei Zhou, Mingjie Sun, Fengru Zhou, Guobo Deng, Yuan Yang* andYun Liang*,Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2‑Iodobiphenyls andα‑Oxocarboxylic Acids,Org. Lett.2021, 23, 7150.
9.Liwei Zhou, Shujia Qiao, Fengru Zhou, Xinyu Xuchen, Guobo Deng, Yuan Yang* andYun Liang*,α‑Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles,Org. Lett.2021,23, 2878.
10.Xiumei Yang, Xiahong Chen, Yankun Xu, Minghao Zhang, Guobo Deng, Yuan Yang* andYun Liang*, Palladium-Catalyzed [4 + 3] or [2 + 2 + 3] Annulation via C-H Activation and Subsequent Decarboxylation: Access to Heptagon-Embedded Polycyclic Aromatic Hydrocarbons,Org. Lett.2021,23, 2610.
11.Liwei Zhou, Xiaodong Liu, Haiyan Lu, Guobo Deng,Yun Liang* Yuan Yang* and Jin-Heng Li*,Copper-catalyzed [3 + 2]/[3 + 2] carboannulation of dienynes and arylsulfonyl chlorides enabled by Smiles rearrangement: access to cyclopenta[a]indene-fused quinolinones,Org. Chem. Front.2021,8, 5092.
12.Mingjie Sun, Xinyang Chen, Zichao Feng, Guobo Deng, Yuan Yang* andYun Liang*,A Catellani and retro-Diels–Alder strategy to access 1-amino phenanthrenes via ortho- and interannular C–H activation of 2-iodobiphenyls,Org. Chem. Front.2021, 8, 6535.
13.Liang Chen Xinyu Xuchen, Fei Wang Yuan Yang, Guobo Deng*, Yilin Liu * andYun Liang*, Double C–S bond formation via multiple Csp3–H bond cleavage: synthesis of 4-hydroxythiazoles from amides and elemental sulfur under metalfree conditions,Org. Biomol. Chem.,2021,19, 10068.
14.Xiai Luo, Wenguang Li, Haiyan Lu, Guobo Deng, Yuan Yang*, Chunming Yang* andYun Liang*, Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring,Chinese Chemical Letters2021,32, 713.
15.Haiyan Lu, Xiumei Yang, Liwei Zhou, Wenguang Li, Guobo Deng, Yuan Yang* andYun Liang*, 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.
16.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.
17.Yuzhong Yang, Liwei Zhou, Xiumei Yang, Xiai Luo, Guobo Deng, Yuan Yang*,Yun Liang*, Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids,Synthesis2020,52, 1223.
18.Wenguang Li, Chao Zhang, Haiyan Lu, Yajun Wang, Guobo Deng,Yun Liang* and Yuan Yang*, Pd-Catalyzed one-pot synthesis of vinylsilanes via a three-component tandem reaction.Org. Chem. Front.2020,7, 2075.
19.Xiai Luo, Liwei Zhou, Haiyan Lu, Guobo Deng,Yun Liang*, Chunming Yang*,and Yuan Yang*, Palladium-Catalyzed Domino Heck/C-H Activation/Decarboxylation: A Rapid Entry to Fused Isoquinolinediones and Isoquinolinones,Org.Lett.2019,21, 9960.
20.Wenguang Li,Wenqi Chen, Bang Zhou,Yankun Xu,Guobo Deng,Yun Liang* and Yuan Yang*,NBE-Controlled Palladium-Catalyzed Interannular Selective C−H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2- Acetamides,Org. Lett.2019,21, 2718.
21.Xiumei Yang,Haiyan Lu,Xiaoming Zhu,Liwei Zhou,Guobo Deng,Yuan Yang* andYun Liang*,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.
22.Liang Chen, Hao Min, Weilan Zeng, Xiaoming Zhu,Yun Liang*,Guobo Deng*andYuan Yang*, 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.
23.Yuzhong Yang, Bang Zhou, Xiaoming Zhu, Guobo Deng,Yun Liang*andYun Yang*, Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C−H Activation and Decarboxylation,Org. Lett.2018,20, 5402.
24.Xiao Luo, Yankun Xu, Genhua Xiao, Wenjuan Liu, Cheng Qian, Guobo Deng, Jianxin Song,Yun Liang*andChunming Yang*, Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C−H Activation,Org. Lett.2018,20, 2997.
25.Xiaoming Zhu, Wenguang Li, Xiao Luo, Guobo Deng,Yun Liang*andJianbin Liu*, A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from o-iodoanilines, DMSO and potassium sulfide,Green Chem.2018,20, 1970.
26.Wenguang Li, Genhua Xiao, Guobo DengandYun Liang*,Pd-Catalyzed disilylation: an efficient route to 2,2’-bis(trimethylsilyl)biphenyls via trapping transient dibenzopalladacyclopentadienes with hexamethyldisilane,Org. Chem. Front.2018,5, 1488.
27.Genhua Xiao, Liang Chen, Bang Zhou, Guobo Deng, Jun GongandYun Liang*,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.
28.Yankun Xu, Xiaodong Liu, Wenqi Chen, Guobo Deng,Yun Liang*andYuan Yang*, Palladium/Norbornene Chemistry: Synthesis of Norbornene-Containing Arylsilanes Involving Double C−Si Bond Formation,J. Org. Chem.2018,83, 13930.
29.Zhilei Zheng, Liang Chen, Cheng Qian, Xiaoming Zhu, Xiumei Yang, Jianbin Liu*, Yuan Yang*andYunLiang*,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.
30.Bang Zhou, Wenqi Chen, Yuzhong Yang, Yuan Yang, Guobo Deng*andYun Liang*,A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates,Org. Biomol. Chem.2018,16, 7959.
31.Genhua Xiao, Hao Min, Zhilei Zheng, Guobo Deng*andYunLiang*,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.
32.Genhua Xiao, Liang Chen, Guobo Deng, Jianbin Liu*andYun Liang*,Disilylation of N-(2-Halophenyl)-2-phenylacrylamides with hexamethyldisilane via trapping the spirocyclic palladacycles,Tetrahedron Lett.2018,58, 1836.
33.Xiaodong Liu, Guobo Deng*andYun Liang*,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.
34.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.
35.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.
36.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.
37.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.
38.Zhou, S.; Xia, G.;Liang, Y.*Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides,Tetrahedron, Lett.2017,58, 338.
39.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.
40.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.
41.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.
42.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.
43.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.
44.Yang, Y.; Huang, H.; Liu, W.;Liang, Y.*Dual Role of Alkynyl Bromides in One-Step Synthesis of Bromo-Substituted Alkynyl Sulfides,Synthetic Communications2015,45, 86.
45.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.
46.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.
47.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.
48.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.
49.Zeng, W.; Dang, P.; Zhang, X.;Liang, Y.*; Peng,C.Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide,RSC Adv.2014,4, 31003.
50.Huang, H.; Yang, Y.; Zhang, X.; Zeng, W.Liang, Y.*,Transition-metal-free approach to synthesis of indolines fromN-(ortho-chloromethyl)aryl amides and iodoniumylides,Tetrahedron Lett.2013,54, 6049.
51.Yang, Y.; Huang, H.; Zhang, X.; Zeng, W.;Liang, Y.*,Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides,Synthesis2013,3137.
52.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.
53.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.
54.Liang, Y.; Geng, W.; Wei, J.; Ouyang, K.; Xi, Z.*Palladium-catalyzed SilylC(sp3)-H Bond Activation,Org. Biomol. Chem.2012,10, 1537.
55.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.
56.Zhang, X.; Yang, Y.;Liang, Y.*Palladium-catalyzed double N-arylation to synthesize multisubstituteddibenzoazepine derivatives,Tetrahedron Lett.2012,53, 6406.
57.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.
58.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.
59.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.
60.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 ethanonesChem. Commun.2010, 8183.
61.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.
62.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.
63.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.
64.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.
65.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.
66.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.
67.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.