"Alkene-to-Alkene" Difunctionalization of Enaminones for the Synthesis of Polyfunctionalized Alkenes by Transition-Metal-Free C-H and C-N Bond Transformation

The three-component reactions of enaminones, disulfides, and alcohols for the synthesis of polyfunctionalized alkenes have been realized via the C-H and C-N bond transformation on enaminones. The reactions proceed in a novel "alkene-to-alkene" difunctionalization mode without using any tra...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 47; pp. 8451 - 8456
Main Authors Ye, Jingfeng, Liu, Yunyun, Luo, Jin, Wan, Jie-Ping
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.12.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
1,4-DIFUNCTIONALIZATION
ETHER
PROGRESS
THIOPHENOLS
AMIDATION
1,3-BIS(SILYLOXY)BUTA-1,3-DIENES
TRIFUNCTIONALIZATION
1,2-DIFUNCTIONALIZATION
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Summary:The three-component reactions of enaminones, disulfides, and alcohols for the synthesis of polyfunctionalized alkenes have been realized via the C-H and C-N bond transformation on enaminones. The reactions proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. The application of the alkene products in the synthesis of divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, and isoxazoles, via simple annulation has also been verified.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03353