Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

被引：16

作者：

Jayaraman, Aravindan ^{[1
]}

Lee, Sunwoo ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

TRANS-HYDROFLUORINATION; SELECTIVE SYNTHESIS; FLUORINE; MONOFLUOROALKENES; IODOFLUORINATION; YNAMIDES; ALKENES;

D O I：

10.1021/acs.orglett.9b00597

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of arylalkynoic acids reacted with 1,3-diiodo-5,5-dimethylhydantoin and HF.pyridine in the presence of AgOAc to provide the corresponding 1-fluoro-2,2-diiodovinylarenes in good yields and high regioselectivity. In addition, Pd-catalyzed cross-coupling reaction of 1-fluoro-2,2-diiodovinylarenes afforded diaryl coupling products in the Suzuki reaction and monoaryl coupling products with high stereo-selectivity in the Hiyama reaction. It was found that C-F-activated borylation of fluoroalkenes using Pd catalyst afforded the vinylboranes with good yields.

引用

页码：3485 / 3489

页数：5

共 43 条

[41] Highly Stereoselective Synthesis of Monofluoroalkenes from α-Fluorosulfoximines and Nitrones [J].

Zhang, Wei ;

Huang, Weizhou ;

Hu, Jinbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9858-9861

[42] LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides [J].

Zhao, Xianghu ;

Wu, Mingsheng ;

Liu, Yisen ;

Cao, Song .

ORGANIC LETTERS, 2018, 20 (18) :5564-5568

[43] (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides [J].

Zhu, Guohao ;

Qiu, Shineng ;

Xi, Yang ;

Ding, Yao ;

Zhang, Dongming ;

Zhang, Rong ;

He, Guangke ;

Zhu, Hongjun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (32) :7746-7753

← 1 2 3 4 5 →