Journal of the Chemical Society. Perkin transactions I p. 1741 - 1747 (1996)
Update date:2022-08-02
Topics:
Zhi, Chengxin
Chen, Qing-Yun
The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80°C gave 1:1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2·OH2O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure. Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3·OH2O-bpy bimetal redox system in ethanol at 70-80°C resulted in the formation of iodine-free 1:1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electronrich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.
View MoreContact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Jiangsu Fengshan Group Co., Ltd.
Contact:86-25-86558671
Address:1903,Central International Mansion 105-6 North Zhongshan Road, Nanjing, China
website:http://www.sdowchem.com
Contact:86-135-2193 7483
Address:8-106 taiyue building
SHUNYUANSHENG BIO-PHARMTECH CO., LTD
website:https://www.whsysbio.com
Contact:--
Address:Building 13, Liandong U Valley-Wuhan Economic Innovation Valley, No. 259, Xingsan Road, Shamao Street, Hannan District, Wuhan City, Hubei Province
Shanghai Xinda Pharmaceuticals Co., Ltd.
Contact:86-21-33692333-8008
Address:999 Linxian Road, Jinshan Industrial Park, Shanghai, China
Doi:10.1039/c7cc03902f
(2017)Doi:10.1016/S0040-4020(01)88112-6
(1986)Doi:10.1055/s-0028-1083498
(2008)Doi:10.1055/s-0028-1083549
(2008)Doi:10.1039/P29870000193
(1987)Doi:10.1016/j.tetasy.2008.10.006
(2008)
