TY - JOUR
T1 - 二氟烯醇硅醚作为含氟砌块在构建有机氟化物中的研究进展
AU - Guo, Mengmeng
AU - Yu, Zilun
AU - Chen, Yulan
AU - Ge, Danhua
AU - Ma, Mengtao
AU - Shen, Zhiliang
AU - Chu, Xueqiang
N1 - Publisher Copyright:
© 2022 Chinese Chemical Society & SIOC, CAS.
PY - 2022/11/25
Y1 - 2022/11/25
N2 - Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.
AB - Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.
KW - difluorinated silyl enol ether
KW - difluoroalkylation
KW - fluorinated compounds
KW - fluorine-containing building block
KW - organofluorine chemistry
UR - http://www.scopus.com/inward/record.url?scp=85135936151&partnerID=8YFLogxK
U2 - 10.6023/cjoc202204060
DO - 10.6023/cjoc202204060
M3 - 文献综述
AN - SCOPUS:85135936151
SN - 0253-2786
VL - 42
SP - 3562
EP - 3587
JO - Chinese Journal of Organic Chemistry
JF - Chinese Journal of Organic Chemistry
IS - 11
ER -