Concise Report
Stereospecific Assembly of Trisubstituted Alkenes via Photoinduced Nitrogen-Centered Radical-Triggered C—C Bond Cleavage/Functionalization of Oxime Esters
Yu Bao,
Zhi-Jie Song,
Jin-Long Dai,
Shenghu Yan,
Yue Zhang,
Jia-Yin Wang,
Guigen Li,
Yu Bao
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorZhi-Jie Song
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorJin-Long Dai
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorShenghu Yan
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Yue Zhang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Jia-Yin Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]Search for more papers by this authorGuigen Li
Department of Chemistry and Biochemistry, Texas Tech University, 79409 USA
Search for more papers by this authorYu Bao,
Zhi-Jie Song,
Jin-Long Dai,
Shenghu Yan,
Yue Zhang,
Jia-Yin Wang,
Guigen Li,
Yu Bao
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorZhi-Jie Song
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorJin-Long Dai
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorShenghu Yan
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorCorresponding Author
Yue Zhang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Jia-Yin Wang
School of Pharmacy, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]; [email protected]Search for more papers by this authorGuigen Li
Department of Chemistry and Biochemistry, Texas Tech University, 79409 USA
Search for more papers by this authorComprehensive Summary
A general and convenient photoredox-catalyzed acylation and alkylcyanation of MBH acetates has been established, enabling the assembly of the C(sp2)–C(sp3) bond by a nitrogen-centered radical strategy for the synthesis of trisubstituted alkenes in moderate to excellent chemical yields (48 examples in total). The reaction of MBH acetates with acyl (indanone) oxime esters afforded trisubstituted alkenes containing 1,4-dicarbonyl groups. Interestingly, the use of Eosin Y as a photocatalyst in the catalytic system resulted in the formation of distal cyano group-anchored trisubstituted alkenes via deconstructive functionalization of cycloketone oxime esters. Notably, these resulting 1,4-dicarbonyl compounds could be applied to late-stage transformations, providing important methods for the synthesis of dihydropyridazin-3(2H)-one.
Supporting Information
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Appendix S1: Supporting Information |
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