Organo-photoredox catalyzed defluoroacetalation of α-trifluoromethyl alkenes for synthesis of masked γ,γ-difluoroallylic aldehydes
作者:Pan Xiang、Linying He、Hao Li、Zhongyu Qi、Min Zhang、Qiang Fu、Jun Wei、Xi Du、Dong Yi、Siping Wei
DOI:10.1016/j.tetlet.2020.152369
日期:2020.9
An organo-photoredox catalyzed defluoroacetalation of alpha-trifluoromethyl alkenes with easily accessible glyoxylic acid acetal being the formyl-radical equivalent has been achieved, affording a great variety of masked gamma,gamma-difluoroallylic aldehydes with good yields and varied functionality tolerance. This mild and transition-metal-free protocol not only allows the incorporation of both an acetal functionality and gem-difluoroalkene moiety into one molecule in a single catalytic cycle, but also offers a straightforward access to masked gamma,gamma-difluoroallylic ketones. Furthermore, the applicability of the proposed protocol is demonstrated by the late-stage functionalization of biologically active molecules and versatile derivatization of newly generated products. (C) 2020 Elsevier Ltd. All rights reserved.