Pd-Catalyzed Domino Imidoylation/Heck/C(sp2)–H Cyclization: Isocyanide Relay Strategy toward Tricyclic-Fused Heterocycles Containing an All-Carbon Quaternary Center

• DOI: 10.1021/acs.orglett.0c02503
• Publication Date: 2020-10-14T20:38:15Z
• Authors: Fan Teng; Yan Peng; Xilong Wang; Weiming Hu; Huaanzi Hu; Yimiao He; Shuang Luo; Qiang Zhu
• Keywords: 01 natural sciences; 0104 chemical sciences

A palladium-catalyzed domino process for the quick assembly of tricyclic-fused heterocycles starting from aryl iodides and functionalized isocyanides containing a disubstituted terminal alkene has been developed. The process is triggered by intermolecular isocyanide insertion, followed by Heck-type carbopalladation of the intramolecular alkene moiety and subsequent C(sp2)-H activation. Moreover, an asymmetric version of this reaction could also be realized in good yield with moderate enantioselectivity after preliminary exploration of chiral ligands.