Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones

被引：8
|
作者：
Kim, Dae Young [1 ]
机构：
[1] Soonchunhyang Univ, Dept Chem, Asan 31538, Chungnam, South Korea
来源：
SYNTHETIC COMMUNICATIONS | 2019年 / 49卷 / 17期
基金：
新加坡国家研究基金会;
关键词：
1,2-Alkyl migration; 1-(1-arylvinyl)cyclobutanols; benzeneselenyl bromide; selenylation; semipinacol rearrangement; VISIBLE-LIGHT PHOTOREDOX; ASYMMETRIC-SYNTHESIS; SEMIPINACOL REARRANGEMENT; MIGRATION SEQUENCES; ELECTROPHILIC CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; RING EXPANSION; KETO ACIDS; TETRAHYDROQUINOLINES; SELENIDES;
D O I：
10.1080/00397911.2019.1616762
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and practical strategy to access beta-selenated cyclic ketone derivatives through the catalyst-free selenylation and semipinacol rearrangement sequence of 1-(1-arylvinyl)cyclobutanols was developed. This reaction employs the easily accessible and shelf-stable benzeneselenyl bromide as an electrophilic selenium source, and the reaction has advantages of mild reaction conditions and broad substrate scope. [GRAPHICS] .
引用
收藏
页码：2203 / 2209
页数：7
相关论文
共 50 条
  • [41] Catalyst-free synthesis and mechanical characterization of TaC nanowires
    Wang, Shiliang
    Ma, Liang
    Mead, James Lee
    Ju, Shin-Pon
    Li, Guodong
    Huang, Han
    [J]. SCIENCE CHINA-PHYSICS MECHANICS & ASTRONOMY, 2021, 64 (05)
  • [42] Catalyst-free synthesis and mechanical characterization of TaC nanowires
    Shiliang Wang
    Liang Ma
    James Lee Mead
    Shin-Pon Ju
    Guodong Li
    Han Huang
    [J]. Science China Physics, Mechanics & Astronomy, 2021, 64
  • [43] Catalyst-free synthesis of α,α-disubstituted carboxylic acid derivatives under ambient conditions via a Wolff rearrangement reaction
    Ji, Xin
    Zhang, Zhikun
    Wang, Yuzhu
    Han, Yazhe
    Peng, Huiling
    Li, Fangzhu
    Liu, Lu
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6916 - 6922
  • [44] Microwave Assisted Catalyst-free Synthesis of Bioactive Heterocycles
    Banerjee, Bubun
    Kaur, Gurpreet
    [J]. CURRENT MICROWAVE CHEMISTRY, 2020, 7 (01) : 5 - 22
  • [45] Catalyst-free synthesis and shape control of CdTe nanowires
    Jin, Xiaoping
    Kruszynska, Marta
    Parisi, Juergen
    Kolny-Olesiak, Joanna
    [J]. NANO RESEARCH, 2011, 4 (09) : 824 - 835
  • [46] Catalyst-Free, Three-Component Synthesis of Amidinomaleimides
    Swift-Ramirez, Wyatt R.
    Whalen, Lindsay A.
    Thompson, Lia K.
    Shoemaker, Kaylee E.
    Rubio, Aris R.
    Weiss, Gregory A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13756 - 13761
  • [47] CATALYST-FREE GREEN SYNTHESIS OF PHTHALAZINONES AT ROOM TEMPERATURE
    Lv, Kang
    Xie, Zixi
    Chen, Xi
    Yao, Weiwei
    Ma, Mengtao
    [J]. HETEROCYCLES, 2023, 106 (01) : 135 - 149
  • [48] Catalyst-free Multicomponent Synthesis of β-Mercapto Diketones in Water
    Li Li
    Liu Bokai
    Wu Qi
    Lin Xianfu
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (09) : 1856 - 1862
  • [49] Catalyst-free synthesis and mechanical characterization of TaC nanowires
    Shiliang Wang
    Liang Ma
    James Lee Mead
    Shin-Pon Ju
    Guodong Li
    Han Huang
    [J]. Science China(Physics,Mechanics & Astronomy), 2021, 64 (05) : 47 - 57
  • [50] Synthesis of silica microcoils by catalyst-free carbothermic method
    Du, Hongli
    Zheng, Chunrui
    [J]. JOURNAL OF NON-CRYSTALLINE SOLIDS, 2011, 357 (21) : 3598 - 3601
12345