Palladium-Catalyzed [3+2+1]/[4+2] Heteroannulation of Allylamines with CO and 1,4-Enynes Leading to 1,7,8,8a-Tetrahydroisoquinolin-3(2H)-ones
Qi Xue , Yang Li , Fu-Jin Sun , Ming Hu , Hu Cai , Jin-Heng Li
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (15) : 1819 -1823.
Palladium-Catalyzed [3+2+1]/[4+2] Heteroannulation of Allylamines with CO and 1,4-Enynes Leading to 1,7,8,8a-Tetrahydroisoquinolin-3(2H)-ones
Aminocarbonylative heteroannulation of unsaturated hydrocarbons with amines and CO has become a key transformation in organic synthesis to build N-heterocycles. In this report, a new palladium-catalyzed aminocarbonylative [3+2+1]/[4+2] heteroannulation of allylamines with CO and 4-en-1-yn-3-yl acetates for the synthesis of 1,7,8,8a-tetrahydroisoquinolin-3(2H)-ones has been developed. The method enables the construction of two new six-membered rings in a single reaction step leading to the formation of the isoquinolinone scaffolds, featuring excellent selectivity, good functional group compatibility and broad substrate scope. A possible mechanism involving Pd-catalyzed isomerization to form the allenyl-Pd intermediate, aminocarbonylation and cycloaddition was proposed.
Palladium / Heteroannulation / Allylamines / 1,4-Enynes / Carbon monoxide / Carbonylation / Multicomponent reactions / Cycloaddition
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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