TY - JOUR
T1 - Accessing Illusive e Isomers of α-Ester Hydrazones via Visible-Light-Induced Pd-Catalyzed Heck-Type Alkylation
AU - Kvasovs, Nikita
AU - Gevorgyan, Vladimir
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/6/17
Y1 - 2022/6/17
N2 - A visible-light-induced Pd-catalyzed stereoselective synthesis of alkylated ester hydrazones has been developed. This method operates via generation of a nucleophilic carbon-centered radical from alkyl bromide, iodide, or redox-Active ester, followed by its addition to hydrazone, and a subsequent desaturation by palladium. The majority of products have E configuration, which are inaccessible by conventional condensation methods. In addition, a sequential C,N-Alkylation protocol has been developed: A reaction between 1,3-dihalides and glyoxylate-derived hydrazone, delivering tetrahydropyridazines.
AB - A visible-light-induced Pd-catalyzed stereoselective synthesis of alkylated ester hydrazones has been developed. This method operates via generation of a nucleophilic carbon-centered radical from alkyl bromide, iodide, or redox-Active ester, followed by its addition to hydrazone, and a subsequent desaturation by palladium. The majority of products have E configuration, which are inaccessible by conventional condensation methods. In addition, a sequential C,N-Alkylation protocol has been developed: A reaction between 1,3-dihalides and glyoxylate-derived hydrazone, delivering tetrahydropyridazines.
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U2 - 10.1021/acs.orglett.2c01409
DO - 10.1021/acs.orglett.2c01409
M3 - Article
C2 - 35653178
AN - SCOPUS:85131966278
SN - 1523-7060
VL - 24
SP - 4176
EP - 4181
JO - Organic Letters
JF - Organic Letters
IS - 23
ER -