1,8-Diazabicyclo[5.4.0]undec-7-ene-Catalyzed Carbonylative Cyclization of Propargylic Alcohols with Elemental Sulfur

被引:11
|
作者
Hu, Yuya [1 ]
Yin, Zhiping [1 ]
Werner, Thomas [1 ]
Spannenberg, Anke [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Zhejiang, Peoples R China
关键词
Carbonylation; Cyclization; Sulfur; Heterocycles; Alkynes; CARBON-MONOXIDE; CATALYZED CARBONYLATION; ASSISTED CARBONYLATION; PRACTICAL SYNTHESIS; BOND FORMATION; AMINES; DERIVATIVES; 1,3-OXATHIOLAN-2-ONES; HETEROCYCLES; EPOXIDES;
D O I
10.1002/ejoc.201701813
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A carbonylation procedure involving the cyclization of propargylic alcohols with elemental sulfur was developed. With 1,8-diazabicyclo[5.4.0]undec-7-ene as the catalyst, elemental sulfur and carbon monoxide are activated and incorporated into propargylic alcohols. Good to excellent yields of the desired sulfur-containing heterocycles were obtained at room temperature.
引用
收藏
页码:1274 / 1276
页数:3
相关论文
共 50 条
  • [21] MICHAEL-TYPE ADDITION OF 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE TO DIMETHYL ACETYLENEDICARBOXYLATE
    MA, LF
    DOLPHIN, D
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (22) : 2251 - 2252
  • [22] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Decomposition of Difluorocarbene and the Subsequent Trifluoromethylation
    Zheng, Jian
    Lin, Jin-Hong
    Deng, Xiao-Yun
    Xiao, Ji-Chang
    ORGANIC LETTERS, 2015, 17 (03) : 532 - 535
  • [23] Syntheses of guanidinoglycosides with the inventive use of Mitsunobu conditions and 1,8-diazabicyclo[5.4.0]undec-7-ene
    Lin, Peishan
    Cher Hui Heng, Sabrina
    Sim, Mui Mui
    Synthesis, 2003, (02) : 255 - 261
  • [24] USE OF 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE IN PREPARATION OF TRIMETHYLSILYL ENOL ETHERS AND TRIMETHYLSILYLACETYLENES
    TANIGUCHI, Y
    INANAGA, J
    YAMAGUCHI, M
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (10) : 3229 - 3230
  • [25] Synthesis and spectrophotometric study of deprotonation of octamethylporphyrin derivatives with 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile
    Yu. B. Ivanova
    Dao The Nam
    A. V. Glazunov
    A. S. Semeykin
    S. G. Pukhovskaya
    N. Zh. Mamardashvili
    Russian Journal of General Chemistry, 2014, 84 : 103 - 107
  • [26] Transition-Metal-Free Poly(thiazolium) lodide/1,8-Diazabicyclo[5.4.0]undec-7-ene/Phenazine-Catalyzed Esterification of Aldehydes with Alcohols
    Chun, Supill
    Chung, Young Keun
    ORGANIC LETTERS, 2017, 19 (14) : 3787 - 3790
  • [27] 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as ligand for atom transfer radical polymerization (ATRP)
    Fournier, D
    Romagné, ML
    Pascual, S
    Montembault, W
    Fontaine, L
    EUROPEAN POLYMER JOURNAL, 2005, 41 (07) : 1576 - 1581
  • [28] Adducts of Rhodium(II) Acetate and Rhodium(II) Pivalate with 1,8-Diazabicyclo[5.4.0]undec-7-ene
    Fussell, Eric D.
    Darko, Ampofo
    CRYSTALS, 2021, 11 (05)
  • [29] Alkaline hydrolysis of poly (ethylene terephthalate) using 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU)
    Forouzeshfar, Fahimeh
    Abedsoltan, Hossein
    Coleman, M. R.
    Lawrence, Joseph G.
    POLYMER DEGRADATION AND STABILITY, 2024, 225
  • [30] MECHANISM OF FORMATION OF PHOSPHONATE CARBANIONS WITH THE USE OF A LITHIUM SALT AND 1,8-DIAZABICYCLO [5.4.0] UNDEC-7-ENE
    FROMENT, F
    CORSET, J
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (11) : 746 - 750