Three-component diels-alder reaction through palladium carbene migratory insertion enabled dearomative C(sp3)-H bond activation

Yiman Mi, Shuoyue Liu, Lingfei Hu, Yihua Wang, Renhui Luo, Yinghua Yu, Zhiyang Zhang, Shan Yuan, Gang Lu () and Xueliang Huang ()
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Yiman Mi: Hunan Normal University
Shuoyue Liu: Hunan Normal University
Lingfei Hu: Shandong University
Yihua Wang: Hunan Normal University
Renhui Luo: Hunan Normal University
Yinghua Yu: Chinese Academy of Sciences
Zhiyang Zhang: Hunan Normal University
Shan Yuan: Hunan Normal University
Gang Lu: Shandong University
Xueliang Huang: Hunan Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract Owning to the versatile nature in participation of Diels-Alder (D-A) reactions, the development of efficient approaches to generate active ortho-quinodimethanes (o-QDMs) has gained much attention. However, a catalytic method involving coupling of two readily accessible components to construct o-QDMs is lacking. Herein, we describe a palladium carbene migratory insertion enabled dearomative C(sp3)-H activation to form active o-QDM species through the cross-coupling of N-tosylhydrazones with aryl halides. The in situ generated o-QDM intermediates were trapped efficiently by 3-nitroindoles and N-sulfonylaldimines to provide dihydroindolo[2,3-b]carbazole derivatives and indole alkaloids modularly. To our knowledge, this reaction represents a rare example on three-component D-A cycloaddition through in situ generation of conjugated dienes by the coupling two readily available materials. We anticipate such a reaction mode could find broad application on diversity oriented six-membered ring construction. Deuterium labeling experiments and density functional theory calculations support a pathway through reversible C(sp3)-H activation to generate heterocyclic o-QDMs.

Date: 2024
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DOI: 10.1038/s41467-024-55190-1

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