TY - JOUR
T1 - Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario
T2 - 1,2-Aminoalkylation and beyond
AU - Shing Cheung, Kelvin Pak
AU - Kurandina, Daria
AU - Yata, Tetsuji
AU - Gevorgyan, Vladimir
N1 - Funding Information:
We thank the National Institutes of Health (GM120281), National Science Foundation (CHE-1936422), and Welch Foundation (Chair, AT-0041) for financial support.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/6/3
Y1 - 2020/6/3
N2 - A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.
AB - A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.
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U2 - 10.1021/jacs.0c03993
DO - 10.1021/jacs.0c03993
M3 - Article
C2 - 32406231
AN - SCOPUS:85085908493
SN - 0002-7863
VL - 142
SP - 9932
EP - 9937
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 22
ER -