Photosensitizer and H-atom Transfer Agent Synergistically Catalyze the Formylation of Fluoroalkyl Imines
作者单位：School of Chemistry and Chemical Engineering Huazhong University of Science and Technology
会议名称：《中国化学会·第十三届全国物理有机化学学术会议》
会议日期：2019年
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
关 键 词：Visible-light-enabled Synergistic catalysis Redox-neutral Fluorinated amino aldehydes
摘 要：β-Aminoalcohols are ubiquitous structural motifs in natural and pharmaceutical compounds. Their fluorinated analogs could find great potentials in drug discovery due to the unique electronic, lipophilic and metabolic properties.1 Nonetheless, the difficulties in synthesizing β-fluoroalkyl β-amino alcohols have undoubtedly limited the researches in this area. α-Amino aldehydes are versatile precursors to different β-amino alcohols. Therefore, a general synthetic method of fluoroalkyl α-amino aldehydes is highly desirable. Our group has recently reported an efficient addition of 1,3-dioxolanes to imines through a radical chain fashion.2 However, this method was inefficient when applied to fluoroalkyl imines. To tackle these problems, a visible-light-enabled catalytic formylation of fluoroalkyl imines is developed. This method provides a general approach to masked fluoroalkyl amino aldehydes. A synergistic catalytic effect between the photosensitizer and the H-atom transfer agent was proven pivotal to this transformation. The product could be converted to various β-fluoroalkyl β-amino alcohols, which are attractive building blocks in the synthesis of bioactive and pharmaceutical compounds.