N-Heterocyclic carbene palladium-catalyzed cascade annulation/alkynylation of 2-alkynylanilines with terminal alkynes

被引:27
作者
Li, Jianxiao [1 ]
Li, Can [1 ]
Ouyang, Lu [1 ]
Li, Chunsheng [1 ]
Wu, Wanqing [1 ]
Jiang, Huanfeng [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ALKYNYLATION; CARBOXYLIC-ACIDS; DECARBOXYLATIVE ALKYNYLATION; SONOGASHIRA REACTIONS; PHOTOREDOX CATALYSIS; MOLECULAR-OXYGEN; C(SP(3))-H BONDS; ROOM-TEMPERATURE; GAMMA-LACTONES; BETA-CARBOLINE;
D O I
10.1039/c7ob01889d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward and highly effective N-heterocyclic carbene-palladium catalyzed cascade annulation/alkynylation of 2-alkynylanilines with terminal alkynes has been enabled to afford free (NH)-3-alkynylindole derivatives in moderate to good yields. This protocol features mild conditions, broad substrate scope, and high atom-and step- economy. Notably, the resultant 3-alkynylindoles could be conveniently transformed into a variety of functionalized indole scaffolds, thus illustrating their potential applications in synthetic and pharmaceutical chemistry.
引用
收藏
页码:7898 / 7908
页数:11
相关论文
共 35 条
[21]   N-heterocyclic carbene enabled rhodium-catalyzed ortho C(sp2)-H borylation at room temperature [J].
Zhong, Lei ;
Zong, Zhi-Hong ;
Wang, Xi-Cun .
TETRAHEDRON, 2019, 75 (17) :2547-2552
[22]   N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids [J].
Wang, Xiao-Xia ;
Luo, Mao-Jun ;
Lu, Jian-Mei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (47) :11438-11444
[23]   Copper-catalyzed direct oxidative annulation of N-iminopyridinium ylides with terminal alkynes using O2 as oxidant [J].
Ding, Shengtao ;
Yan, Yuepeng ;
Jiao, Ning .
CHEMICAL COMMUNICATIONS, 2013, 49 (39) :4250-4252
[24]   Palladium(II) complexes of imidazolin-2-ylidene N-heterocyclic carbene ligands with redox-active dimethoxyphenyl or (hydro)quinonyl substituents [J].
Berben, Louise A. ;
Craig, Donald C. ;
Gimbert-Surinach, Carolina ;
Robinson, Andrew ;
Sugiyarto, Kristian H. ;
Colbran, Stephen B. .
INORGANICA CHIMICA ACTA, 2011, 370 (01) :374-381
[25]   Carbazole-Based N-Heterocyclic Carbenes for the Promotion of Copper-Catalyzed Palladium-Free Homo-/Hetero-Coupling of Alkynes and Sonogashira Reactions [J].
Girase, Tejpalsingh Ramsingh ;
Bhilare, Shatrughn ;
Bandaru, Siva Sankar Murthy ;
Chrysochos, Nicolas ;
Schulzke, Carola ;
Sanghvi, Yogesh S. ;
Kapdi, Anant R. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) :274-291
[26]   A Highly Substitutable Palladium(II) Complex Stabilized by the Smallest Steric N-Heterocyclic Carbene, IMe (IMe=1,3-Dimethylimidazole-2-ylidene) [J].
Lee, Eunsung ;
Bae, Dae Young ;
Yandulov, Dmitry V. .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (11) :1745-1746
[27]   Palladium-Catalyzed C(sp2)-H Olefination/Annulation Cascades of Aryl Carboxamides Assisted by N,S-Bidentate Auxiliary [J].
Li, Ling ;
Zhang, Xing-Guo ;
Zhang, Xiao-Hong .
SYNTHESIS-STUTTGART, 2019, 51 (16) :3077-3084
[28]   Catalytic activities in the direct C5 arylation of novel palladium N-heterocyclic carbene complexes containing benzimidazol-2-ylidene nucleus [J].
Akkoc, Senem ;
Gok, Yetkin ;
Akkurt, Mehmet ;
Tahir, Muhammad Nawaz .
INORGANICA CHIMICA ACTA, 2014, 413 :221-230
[29]   Preparation and characterization of PEPPSI-palladium N-heterocyclic carbene complexes using benzimidazolium salts catalyzed Suzuki-Miyaura cross coupling reaction and their antitumor and antimicrobial activities [J].
Boubakri, Lamia ;
Dridi, Khaireddine ;
Al-Ayed, Abdullah Sulaiman ;
Ozdemir, Ismail ;
Yasar, Sedat ;
Hamdi, Naceur .
JOURNAL OF COORDINATION CHEMISTRY, 2019, 72 (03) :516-527
[30]   Direct C-H Bond Arylation of C2-Blocked Pyrrole with Aryl Halides Using Palladium(II)-N-Heterocyclic Carbene Catalysts [J].
Kaloglu, Murat ;
Kaloglu, Nazan ;
Ozdemir, Ismail .
CHEMISTRYSELECT, 2018, 3 (20) :5600-5607