Recycle Waste Salt as Reagent: A One-Pot Substitution/Krapcho Reaction Sequence to α-Fluorinated Esters and Sulfones

被引:37
作者
Zhu, Feng [1 ]
Xu, Peng-Wei [1 ]
Zhou, Feng [1 ]
Wang, Cui-Hong [1 ]
Zhou, Jian [1 ,2 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
RADICAL-MEDIATED CLEAVAGE; BETA-AMINO ESTERS; CATALYST-FREE; ENANTIOSELECTIVE MONOFLUOROMETHYLATION; HIGHLY EFFICIENT; ATOM EFFICIENCY; WITTIG REACTION; FLUORO ESTERS; ACID; DIFLUOROENOXYSILANES;
D O I
10.1021/acs.orglett.5b00072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A "one-pot" tandem substitution/Krapcho reaction is reported for the facile synthesis of alpha-fluorinated esters and sulfones, which utilizes the byproduct salt formed in the substitution step as an indispensible reagent to facilitate the Krapcho reaction step. This represents the first sustainable tandem reaction that internally recycles the waste salt formed in the upstream step as the reagent for the downstream step.
引用
收藏
页码:972 / 975
页数:4
相关论文
共 76 条
[71]   Highly Efficient "On Water" Catalyst-Free Nucleophilic Addition Reactions Using Difluoroenoxysilanes: Dramatic Fluorine Effects [J].
Yu, Jin-Sheng ;
Liu, Yun-Lin ;
Tang, Jing ;
Wang, Xin ;
Zhou, Jian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9512-9516
[72]   Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group [J].
Zhao, Yanchuan ;
Gao, Bing ;
Ni, Chuanfa ;
Hu, Jinbo .
ORGANIC LETTERS, 2012, 14 (23) :6080-6083
[73]  
Zhou J, 2014, MULTICATALYST SYSTEM, V9
[74]   Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions [J].
Zhou, Jian .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) :422-434
[75]  
Zhou L., 2014, J ORG CHEM FRONT, V1, P172
[76]   A Facile Method for the Synthesis of 3-Substituted 3-(Alkylthio)oxindoles or 3-Alkoxyoxindoles [J].
Zhu, Feng ;
Zhou, Feng ;
Cao, Zhong-Yan ;
Wang, Chao ;
Zhang, Yong-Xue ;
Wang, Cui-Hong ;
Zhou, Jian .
SYNTHESIS-STUTTGART, 2012, 44 (20) :3129-3144