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Chelation-assisted iridium-catalyzed hydroalkenylation and hydroarylation/cyclization with conjugated trienes.

Yilei LiaoCheng ZhangYini WangYibu HuLiyuan DingLiangjun ZhongGuofu ZhongJian Zhang
Published in: Organic & biomolecular chemistry (2023)
Iridium-catalyzed hydroalkenylation of conjugated trienes by chelation-assisted alkenyl C-H activation of acrylamides has been demonstrated to produce 1,4,6-trienes atom efficiently with excellent regio - and E / Z selectivities. In contrast, the reaction of benzamides and 1,3,5-trienes proceeds by a tandem hydroarylation of the trienes and cyclization via intramolecular 1,2-addition, providing valuable trans -tetrahydroisoquinolinone derivatives. A broad range of aromatic and aliphatic 1,3,5-trienes bearing various functionalities were compatible to deliver target products with high yields and E / Z selectivity. The successful gram-scale preparation and selective hydrogenation to give the alkylation product further demonstrates the practicability of this protocol to potential applications.
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