Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway
Kenzo Yahata, Shu Sakurai, Shuhei Hori, Shin Yoshioka, Yuki Kaneko, Kai Hasegawa, Shuji Akai
Abstract
Herein, we describe the generation of an organochromium-type carbanion species from a non-activated C-H bond and its nucleophilic addition to aldehydes. The catalytic carbanion generation occurred through formal deprotonation of a non-activated C-H bond under mild conditions and did not need the prefunctionalization or anion stabilizing group. Carbon radical intermediates generated by decatungstate photocatalyst-mediated hydrogen abstraction were captured by a chromium salt with the reductive radical-polar crossover reaction to produce organochromium carbanions.
Topics & Concepts
CarbanionChemistryDeprotonationNucleophileTriple bondPhotochemistryCatalysisMedicinal chemistryOrganic chemistryDouble bondIonCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions