Efficient synthesis of thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]-indoles by Pd-catalyzed site-selective C-C and C-N coupling reactions

被引:41
|
作者
Tran Quang Hung [1 ]
Tuan Thanh Dang [1 ]
Villinger, Alexander [1 ]
Tran Van Sung [2 ]
Langer, Peter [1 ,3 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Vietnam Acad Sci & Technol, Hanoi, Vietnam
[3] Univ Rostock eV LIKAT, D-18059 Rostock, Germany
关键词
THIN-FILM TRANSISTORS; FIELD-EFFECT TRANSISTORS; FUNCTIONALIZED ACENES; HIGH-MOBILITY; HETEROACENES; TETRABROMOTHIOPHENE; SEMICONDUCTORS;
D O I
10.1039/c2ob26489g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heteroacenes (thieno[3,2-b:4,5-b']diindoles and benzothieno[3,2-b]indoles) were efficiently synthesized from tetrabromothiophene and 2,3-dibromobenzothiophene in two steps, respectively. In the first step, a site-selective Pd-catalyzed C-C coupling is carried out, followed by a two-fold C-N coupling with aromatic and aliphatic amines.
引用
收藏
页码:9041 / 9044
页数:4
相关论文
共 50 条
  • [21] Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C-N bond-forming reaction
    Iaroshenko, Viktor O.
    Ali, Sajid
    Babar, Tariq Mahmood
    Abbasi, Muhammad S. A.
    Sosnovskikh, Vyacheslav Ya
    Villinger, Alexander
    Tolmachev, Andrey
    Langer, Peter
    TETRAHEDRON, 2013, 69 (15) : 3167 - 3181
  • [22] Palladium-Catalyzed C-S Coupling: Access to Thioethers, Benzo[b]thiophenes, and Thieno[3,2-b]thiophenes
    Kuhn, Marius
    Falk, Florian C.
    Paradies, Jan
    ORGANIC LETTERS, 2011, 13 (15) : 4100 - 4103
  • [23] Selective Synthesis of Pyrano[3,2-b]indoles or Cyclopenta[b]indoles Tethered with Medium-Sized Rings via Cascade C-C σ-Bond Cleavage and C-H Functionalization
    Wang, Mengdan
    Yang, Yajie
    Yin, Liqiang
    Feng, Ye
    Li, Yanzhong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 683 - 692
  • [24] Efficient access to β- and γ-carbolines from a common starting material by sequential site-selective Pd-catalyzed C-C, C-N coupling reactions
    Tran Quang Hung
    Do Trung Hieu
    Dinh Van Tinh
    Ha Nam Do
    Tuan Anh Nguyen Tien
    Dang Van Do
    Le Thanh Son
    Ngoc Han Tran
    Nguyen Van Tuyen
    Vu Minh Tan
    Ehlers, Peter
    Tuan Thanh Dang
    Langer, Peter
    TETRAHEDRON, 2019, 75 (40)
  • [25] Domino C-N Bond Formation via a Palladacycle with Diaziridinone. An Approach to Indolo[3,2-b]indoles
    Debnath, Sudarshan
    Liang, Lingli
    Lu, Mei
    Shi, Yian
    ORGANIC LETTERS, 2021, 23 (09) : 3237 - 3242
  • [26] 2-bromo-1-phenylethylidenemalononitrile in synthesis of functionally substituted thieno[3,2-b]pyridines and thiazolo[4,5-b]pyridines
    Ivanov, VL
    Artemov, VA
    Shestopalov, AM
    Nesterov, VN
    Struchkov, YT
    Litvinov, VP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1996, (03): : 413 - 419
  • [27] SYNTHESIS OF PYRROLE, PYRROLIDONE, PYRROLO[3,4-C]PYRAZOLE, PYRROLO[3,2-B]PYRIDINE AND PYRROLO[3,2-B]PYRROLE DERIVATIVES
    ELBANNANY, AAA
    IBRAHIM, LI
    HETEROCYCLES, 1988, 27 (09) : 2071 - 2075
  • [28] FUSED THIOPYRONES .5. SYNTHESES AND REACTIONS OF 3-FORMYL-INDENO[1,2-B]THIOPYRONES, 3-FORMYL-[1]-BENZOFURO[3,2-B]THIOPYRONES, 3-FORMYL-[1]-BENZOTHIENO[3,2-B]THIOPYRONES, AND 3-FORMYL-THIOPYRONO[3,2-B]INDOLES
    GORLITZER, K
    VOGT, R
    ARCHIV DER PHARMAZIE, 1990, 323 (10) : 841 - 846
  • [29] SYNTHESIS AND ANTIALLERGY ACTIVITY OF 4-OXOPYRANO[3,2-B]INDOLES
    UNANGST, PC
    BROWN, RE
    HERZIG, DJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (11) : 1251 - 1255
  • [30] Thieno[3,2-b]thiophene-Bridged D-π-A Polymer Semiconductor Based on Benzo[1,2-b:4,5-b′]dithiophene and Benzoxadiazole
    Wang, Xiaochen
    Jiang, Pei
    Chen, Yu
    Luo, Hao
    Zhang, Zhiguo
    Wang, Haiqiao
    Li, Xiaoyu
    Yu, Gui
    Li, Yongfang
    MACROMOLECULES, 2013, 46 (12) : 4805 - 4812