Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C–H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones

Manman Sun; Jinshan Li; Weida Chen; Haijian Wu; Jianguo Yang; Zhiming Wang

doi:10.1055/s-0039-1690219

Synthesis, Table of Contents

Synthesis 2020; 52(08): 1253-1265
DOI: 10.1055/s-0039-1690219

special topic

Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C–H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones

Manman Sun

,

Jinshan Li

,

Weida Chen

,

Haijian Wu

,

Jianguo Yang

,

Zhiming Wang∗

Abstract

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Published as part of the Special Topic Domino C–H Functionalization Reaction/Cascade Catalysis

Abstract

Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides with 1,3-dienes via C–H functionalization is developed using air as the terminal oxidant. The method demonstrates good functional group tolerance and high stereoselectivity, affording a series of 3,4-dihydroisoquinolones and 5,6-dihydropyridinones in yields of up to 99%.

Key words

palladium - [4+2] annulation - carboxamides - dienes - C–H functionalization - 3,4-dihydroisoquinolones - 5,6-dihydropyridinones

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References

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