Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents

作者:Chen, X (Chen, Xiang)[ 1 ] ; Gong, XX (Gong, Xingxing)[ 1 ] ; Li, ZY (Li, Zhengyu)[ 1 ] ; Zhou, G (Zhou, Gang)[ 1 ] ; Zhu, ZH (Zhu, Zhihong)[ 1 ] ; Zhang, WL (Zhang, Weilu)[ 1 ] ; Liu, SS (Liu, Shanshan)[ 1 ] ; Shen, X (Shen, Xiao)[ 1 ]

NATURE COMMUNICATIONS

卷: 11 期: 1

文献号: 2756

DOI: 10.1038/s41467-020-16380-9

出版年: JUN 2 2020

文献类型:Article

摘要

Trifluoroethanol and difluoroethanol units are important motifs in bioactive molecules, but the methods to direct incorporate these units are limited. Herein, we report two organosilicon reagents for the transfer of trifluoroethanol and difluoroethanol units into molecules. Through intramolecular C-Si bond activation by alkoxyl radicals, these reagents were applied in allylation, alkylation and alkenylation reactions, enabling efficient synthesis of various tri(di)fluoromethyl group substituted alcohols. The broad applicability and general utility of the approach are highlighted by late-stage introduction of these fluoroalkyl groups to complex molecules, and the synthesis of antitumor agent Z and its difluoromethyl analog Z'.

关键词

KeyWords Plus:CARBONYL-COMPOUNDS; BOND; TRIFLUOROMETHYLATION; FUNCTIONALIZATION; FLUORINE; REACTIVITY; OXINDOLES; KETONES; ALKENES; AZIDES

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Inst Adv Studies, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Peoples R China.

通讯作者地址: Shen, X (通讯作者)

Wuhan Univ, Inst Adv Studies, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Inst Adv Studies, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Peoples R China

电子邮件地址:xiaoshen@whu.edu.cn