Fluoroalkylation of trimethylsilyl enol ether of pinacolone under ultraviolet irradiation

Abstract

UV irradiation of CH2:C(OSiMe3)CMe3 (I) with equal mole of CF3CBr3 gave a mixture of Me3SiBr, CF3CBr2CH2COCMe3 (II), CF3CBr:CHCOCMe3 (III) and pinacolone. I also reacted with Cl(CF2)nI (n = 2, 4, 6) under similar condition to give the fluorinated ketone, Cl(CF2)nCH2COCMe3 (IV) and Me3SiI resp. Treatment of compounds II and IV with aqueous NaHCO3 or NaOH furnished the corresponding a,b-enone III and Cl(CF2)n-1CF:CHCOCMe3 in good yield.

Key words: DIMETHYL GROUP, ETHER, HALOHYDROCARBON, ORGANO SILICON COMPOUNDS, ENOLS, ULTRAVIOLET RADIATION, BUTANONE P, TRIMETHYL GROUP, HALOTHANE P, FLUOROALKYLATION

CLC Number:

O621

Cite this article

ZHANG LONGQING;HUANG WEIYUAN. Fluoroalkylation of trimethylsilyl enol ether of pinacolone under ultraviolet irradiation[J]. Chin. J. Org. Chem., 1989, 9(1): 38-40.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Lingna Wang, Xiaoqing Liu, Gang Lin, Hongying Jin, Minjun Jiao, Xuefen Liu, Shuping Luo. Photocatalytic Activation of C(sp³)—H Bonds to Form C—S Bonds Catalyzed by (Oxybis(4,1-phenylene))bis(phenylmethanone) [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2848-2854.
[2]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[3]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[4]	Xiantao Ma, Xiaoyu Yan, Yingying Zhu, Shuanglin Niu, Yuxuan Wang, Chao Yuan. Water-Promoted Green Synthesis of Heteroaryl Thioether [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2136-2142.
[5]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[6]	Hao Zhang, Qingbin Zhao, Zhongrui Ruan, Zhenxing Liu. Recent Development of SuFEx Reaction between Silyl Ethers and Sulfur(VI) Fluoride Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3569-3579.
[7]	Li Xu, Lanlan Lü, Xiangshan Wang. Copper-Catalyzed Synthesis of β-Keto Sulfones from Enol Silyl Ether and Sodium Arylsulfinates [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3644-3651.
[8]	Zhi Tu, Jinsheng Yu, Jian Zhou. Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3491-3507.
[9]	Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu. Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 313-319.
[10]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[11]	Qian Zhang, Yihao Li, Leichuan Xu, Haoyun Ma, Xiangdong Li, Ming'an Wang. Synthesis and Fungicidal Activity of Novel Butenolide Compounds Containing Oxime Ether Moiety [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2438-2448.
[12]	Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu, Guodong Yin. PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2079-2088.
[13]	Xinling Li, Weidong Meng, Xiuhua Xu, Yan'gen Huang. Visible Light Induced Arylfluoroalkylation of Activated Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1820-1830.
[14]	Xiu Wang, Wengui Duan, Guishan Lin, Baoyu Li, Wenjing Zhang, Fuhou Lei. Synthesis, Antifungal Activity, Three-Dimensional Quantitative Structure-Activity Relationship and Molecular Docking Study of 4-Acyl-3-amino-1,2,4-triazole-thioether Derivatives Containing Natural Pinene Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 871-883.
[15]	Yuxi Zhu, Ting Xiao, Dong Xia, Wenchao Yang. Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4067-4077.

非呐酮的烯醇三甲基硅醚在紫外光照下的氟烷基化反应