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

Fan Teng; Yan Peng; Xilong Wang; Weiming Hu; Huaanzi Hu; Yimiao He; Shuang Luo; Qiang Zhu

doi:10.1021/acs.orglett.0c02503

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

Org Lett. 2020 Nov 6;22(21):8188-8192. doi: 10.1021/acs.orglett.0c02503. Epub 2020 Oct 14.

Authors

Fan Teng^{1

2}, Yan Peng^{1

2}, Xilong Wang^{1

2}, Weiming Hu^{1

2}, Huaanzi Hu^{1

2}, Yimiao He³, Shuang Luo^{1

2}, Qiang Zhu^{1

2

3}

Affiliations

¹ State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, China.
² University of Chinese Academy of Sciences, No. 19(A) Yuquan Road, Shijingshan District, Beijing 100049, China.
³ Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning 530001, China.

PMID: 33052680
DOI: 10.1021/acs.orglett.0c02503

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't