Larionova, Natalia A., Miyatake Ondozabal, Jun, Smith, Emily G. and Couso Cambeiro, Jacobo ORCID: 0000-0002-7365-7201 (2021) Letter: A photocatalytic regioselective direct hydroaminoalkylation of aryl-substituted alkenes with amines. Organic Letters, 23 (14). pp. 5383-5388. ISSN 1523-7060 (Print), 1523-7052 (Online) (doi:https://doi.org/10.1021/acs.orglett.1c01715)

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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.

Item Type:	Article
Uncontrolled Keywords:	visible light; photoredox; photocatalysis; α-aminoalkyl radical; electron-deficient alkene; β-amino acid; styrene; regiose-lectivity; DFT; continuous flow; anti-Markovnikov
Subjects:	Q Science > Q Science (General)
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Last Modified:	17 May 2023 13:53
URI:	http://gala.gre.ac.uk/id/eprint/42631

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