Gold-Catalyzed Oxidations of 1,3-Diynamides with C(1) versus C(3) Regioselectivity: Catalyst-Dependent Oxidative Cyclizations in the C(3) Oxidation

This work reports two distinct paths in catalytic oxidations of 1,3-diynamides with 8-methylquinoline oxide. A typical C(1) regioselectivity was observed for aryl-substituted 1,3-diyn-1-amides, whereas an unexpected C(3) regioselectivty occurred for 5-hydroxyl,3-diyn-1-amides. We focused on the C(3)...

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Published inOrganic letters Vol. 22; no. 11; pp. 4478 - 4482
Main Authors Skaria, Manisha, Hsu, Yu-Chen, Jiang, Yan-Ting, Lu, Ming-Yi, Kuo, Tung-Chun, Cheng, Mu-Jeng, Liu, Rai-Shung
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
CYCLOADDITION
CARBENES
COMPLEXES
CONSTRUCTION
CYCLOPROPANATION
C-H FUNCTIONALIZATION
EFFICIENT
ACCESS
TRANSFORMATIONS
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Summary:This work reports two distinct paths in catalytic oxidations of 1,3-diynamides with 8-methylquinoline oxide. A typical C(1) regioselectivity was observed for aryl-substituted 1,3-diyn-1-amides, whereas an unexpected C(3) regioselectivty occurred for 5-hydroxyl,3-diyn-1-amides. We focused on the C(3) oxidations of 5-hydroxyl,3-diyn-1-amides because we observed two oxidative cyclizations of the same substrates to yield 2-aminomethylenefuran-3(2H)-ones and 2-amino-4H-pyran-4-ones using AuCl3 and a cationic gold catalyst, respectively. Density functional theory calculations were performed to rationalize the C(3) regioselectivity on 5-hydroxy1,3-diyn-1-amides.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01480