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
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 10期
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
  • [31] FACILE CONVERSION OF EPOXIDES TO CHLOROHYDRINS WITH TITANIUM(IV) CHLORIDE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE
    SPAWN, CL
    DRTINA, GJ
    WIEMER, DF
    SYNTHESIS-STUTTGART, 1986, (04): : 315 - 317
  • [32] Synthesis and spectrophotometric study of deprotonation of octamethylporphyrin derivatives with 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile
    Ivanova, Yu B.
    Dao The Nam
    Glazunov, A. V.
    Semeykin, A. S.
    Pukhovskaya, S. G.
    Mamardashvili, N. Zh
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (01) : 103 - 107
  • [33] Reaction Mechanism and Kinetics of 1,8-Diazabicyclo[5.4.0]undec-7-ene and Carbon Dioxide in Alkanol Solutions
    Oztuerk, Mustafa C.
    Ume, Cyril S.
    Alper, Erdogan
    CHEMICAL ENGINEERING & TECHNOLOGY, 2012, 35 (12) : 2093 - 2098
  • [34] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): A highly efficient catalyst in glycerol carbonate synthesis
    Munshi, Mudassir K.
    Gade, Swapna M.
    Mane, Manoj V.
    Mishra, Deepti
    Pal, Sourav
    Vanka, Kumar
    Rane, Vilas H.
    Kelkar, Ashutosh A.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 391 : 144 - 149
  • [35] Synthesis of Azobenzenes Using N-Chlorosuccinimide and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)
    John, Alford Antoine
    Lin, Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9873 - 9876
  • [36] 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) as ligand for atom transfer radical polymerization (ATRP)
    Fontaine, L. (laurent.fontaine@univ-lemans.fr), 1600, Elsevier Ltd (41):
  • [37] Mechanism of Palladium-Catalyzed C-N Coupling with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) as a Base
    Kim, Seoung-Tae
    Pudasaini, Bimal
    Baik, Mu-Hyun
    ACS CATALYSIS, 2019, 9 (08): : 6851 - 6856
  • [38] A FACILE CONVERSION OF PRIMARY OR SECONDARY ALCOHOLS WITH N-PERFLUOROBUTANESULFONYL FLUORIDE/1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE INTO THEIR CORRESPONDING FLUORIDES
    BENNUASKALMOWSKI, B
    VORBRUGGEN, H
    TETRAHEDRON LETTERS, 1995, 36 (15) : 2611 - 2614
  • [39] 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition
    Yeom, Chang-Eun
    Kim, Mi Jeong
    Kim, B. Moon
    TETRAHEDRON, 2007, 63 (04) : 904 - 909
  • [40] TRANSESTERIFICATION OF BENZYL PHENYLACETATE USING POLYMERIC QUATERNARY AMMONIUM SALT OF 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE
    ISHIKAWA, T
    OHSUMI, Y
    KAWAI, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (03) : 819 - 824
12345