A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines
Н. И. Ларионова, Jun Miyatake Ondozabal, Emily G. Smith, Xacobe C. Cambeiro
Abstract
A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.
Topics & Concepts
ChemistryRegioselectivityAnilineMarkovnikov's ruleSelectivityPhotocatalysisArylRadicalOrganic chemistryFunctional groupCombinatorial chemistryCatalysisPolymerAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques