1,6-Addition Reactions of Difluoroenol Silyl Ethers with Benzoquinones and Quinonediimines To Access Difluorooxymethyl and Difluoroaminomethyl Compounds

被引:3
作者
Hong, Peng [1 ,2 ,3 ]
Xu, Jinjing [1 ,2 ]
Li, Jinshan [1 ,2 ]
Zhu, Xiaolei [1 ,2 ]
Ying, Anguo [3 ]
Wang, Zhiming [1 ,2 ]
Yang, Jianguo [1 ,2 ]
机构
[1] Taizhou Univ, Adv Res Inst, Jiaojiang 318000, Zhejiang, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut Sci, Jiaojiang 318000, Zhejiang, Peoples R China
[3] Qufu Normal Univ, Dept Chem & Chem Engn, Qufu 273100, Shandong, Peoples R China
关键词
1,6-Addition; Difluoroenol Silyl Ethers; Benzoquinones; Quinonediimines; Hexafluoroisopropanol; ENOL ETHERS; ASYMMETRIC-SYNTHESIS; EFFICIENT; QUINONES; ALCOHOLS; ANALOGS; WATER; SITE;
D O I
10.1002/adsc.202300877
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The etherification and amination of difluoroenol silyl ethers with benzoquinones and quinonediimines were achieved by using hexafluoroisopropanol (HFIP) as the solvent. This 1,6-addition reaction could construct difluorooxymethyl and difluoroaminomethyl compounds under metal-free conditions. It is preliminarily speculated that the reaction took place through a single electron transfer (SET) process. image
引用
收藏
页码:4550 / 4555
页数:6
相关论文
共 10 条
  • [1] Organocatalytic Asymmetric 1,6-Addition Reactions
    Biju, Akkattu T.
    CHEMCATCHEM, 2011, 3 (12) : 1847 - 1849
  • [2] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
    Chauhan, Pankaj
    Kaya, Ugur
    Enders, Dieter
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912
  • [3] Recent developments in 1,6-addition reactions ofpara-quinone methides (p-QMs)
    Wang, Jia-Yin
    Hao, Wen-Juan
    Tu, Shu-Jiang
    Jiang, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (13): : 1743 - 1778
  • [4] Alkoxylation of para-Quinone Methides via Bismuth Complex Catalyzed 1,6-Addition Reactions of Alcohols
    Li, Hanlin
    Liu, Donglan
    Chen, Liang
    Xu, Haiyan
    Lu, Hongfei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3279 - 3284
  • [5] Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: access to functionalized allylsilanes
    Ahmad, Tanveer
    Li, Qi
    Qiu, Sheng-Qi
    Xu, Jian-Lin
    Xu, Yun-He
    Loh, Teck-Peng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) : 6122 - 6126
  • [6] Highly Selective 1,4-and 1,6-Addition of P(O)?H Compounds to p-Quinones: A Divergent Method for the Synthesis of C- and O-Phosphoryl Hydroquinone Derivatives
    Xiong, Biquan
    Shen, Ruwei
    Goto, Midori
    Yin, Shuang-Feng
    Han, Li-Biao
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (52) : 16902 - 16910
  • [7] Phosphine Sequentially Catalyzed Domino 1,6-Addition/Annulation: Access to Functionalized Chromans and Tetrahydroquinolines with an Ethynyl-Substituted All-Carbon Quaternary Center
    Zhu, Yannan
    Wang, Dan
    Huang, You
    ORGANIC LETTERS, 2019, 21 (04) : 908 - 912
  • [8] High diastereoselective synthesis of spiro-isoxazolonechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with unsaturated isoxazolones
    Ye, Zaijun
    Bai, Lijuan
    Bai, Yan
    Gan, Zongjie
    Zhou, Hui
    Pan, Tao
    Yu, Yu
    Zhou, Jing
    TETRAHEDRON, 2019, 75 (05) : 682 - 687
  • [9] Regio- and stereoselective a(4)-umpolung reactions of alpha,beta-unsaturated esters to 1,6-dicarbonyl compounds by addition of enantiopure nucleophiles to racemic tetracarbonyl(eta(3)-allyl)iron(1+) complexes
    Enders, D
    Fey, P
    Schmitz, T
    Lohray, BB
    Jandeleit, B
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 514 (1-2) : 227 - 232
  • [10] Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one
    Shinde, Jivan
    Kavala, Veerababurao
    Yao, Ching-Fa
    ORGANIC LETTERS, 2023, 25 (38) : 6943 - 6948