Formylation of Fluoroalkyl Imines through Visible-Light-Enabled H-Atom Transfer Catalysis: Access to Fluorinated α-Amino Aldehydes

Org Lett. 2019 Apr 5;21(7):2019-2024. doi: 10.1021/acs.orglett.9b00128. Epub 2019 Mar 22.

Abstract

A visible-light-enabled catalytic formylation of fluoroalkyl imines is developed. With readily accessible starting materials and organocatalysts, 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. After removing the mask, free aldehydes can be obtained and further converted to various β-fluoroalkyl β-amino alcohols, which are attractive building blocks in the synthesis of bioactive and pharmaceutical compounds.

Publication types

  • Research Support, Non-U.S. Gov't