Details

Autor(en) / Beteiligte

• Bao, Yu
• Song, Zhi‐Jie
• Dai, Jin‐Long
• Yan, Shenghu
• Zhang, Yue
• Wang, Jia‐Yin
• Li, Guigen

Titel

Stereospecific Assembly of Trisubstituted Alkenes via Photoinduced Nitrogen‐Centered Radical‐Triggered C—C Bond Cleavage/Functionalization of Oxime Esters

Ist Teil von

• Chinese journal of chemistry, 2024-06, Vol.42 (12), p.1399-1406

Ort / Verlag

Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA

Erscheinungsjahr

2024

Quelle

Wiley Blackwell Single Titles

Beschreibungen/Notizen

• Comprehensive 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. 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).