Palladium(II)-Catalyzed Tandem γ-C(sp2)-H Arylation and Cyclization for the Construction of Natural Product-Like Polycyclic Fused ortho-Quinone Scaffolds

Xingjun Li; Yu Chen; Xiong Xie; Jing Li; Jiang Wang; Hong Liu

doi:10.1021/acs.orglett.4c00900

Palladium(II)-Catalyzed Tandem γ-C(sp²)-H Arylation and Cyclization for the Construction of Natural Product-Like Polycyclic Fused ortho-Quinone Scaffolds

Org Lett. 2024 Apr 26;26(16):3407-3412. doi: 10.1021/acs.orglett.4c00900. Epub 2024 Apr 12.

Authors

Xingjun Li^{1

2}, Yu Chen^{2

3}, Xiong Xie^{2

3}, Jing Li^{2

3}, Jiang Wang^{2

4}, Hong Liu^{1

2

3}

Affiliations

¹ School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China.
² State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
³ University of Chinese Academy of Sciences, Beijing 100049, China.
⁴ Lingang Laboratory, Shanghai 200031, China.

PMID: 38607815
DOI: 10.1021/acs.orglett.4c00900

Abstract

Here, we report a novel strategy for the direct construction of polycyclic fused ortho-quinone scaffolds through palladium(II)-catalyzed tandem γ-C(sp²)-H arylation and cyclization of arylglyoxals with aryl iodides. This transformation features unique tandem transient directing of γ-C(sp²)-H arylation and cyclization reaction mode, broad substrate scope, especially for the aromatic substrates containing oxygen and sulfur atoms, and avoiding the common issue of aromatization due to the construction of the hexatomic ring.