Modular Assembly of Spirocarbocyclic Scaffolds through Pd0-Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes
Zhijun Zuo
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
These authors contributed equally to this work.
Search for more papers by this authorHui Wang
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
These authors contributed equally to this work.
Search for more papers by this authorLiangxin Fan
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorJingjing Liu
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorProf. Dr. Yaoyu Wang
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xinjun Luan
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorZhijun Zuo
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
These authors contributed equally to this work.
Search for more papers by this authorHui Wang
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
These authors contributed equally to this work.
Search for more papers by this authorLiangxin Fan
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorJingjing Liu
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorProf. Dr. Yaoyu Wang
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xinjun Luan
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127 China
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorAbstract
A novel palladium(0)-catalyzed dearomatizing [2+2+1] spiroannulation of 1-bromo-2-naphthols with aryl iodides and alkynes was developed for the rapid assembly of spiro[indene-1,1′-naphthalen]-2′-ones. This three-component cascade reaction was realized through consecutive Catellani-type C−H activation, unsymmetrical biaryl coupling, alkyne migratory insertion, and arene dearomatization. The potential utility of our method is illustrated by the one-step construction of the polycyclic skeletons of dalesconols A and B from alkyne-tethered aryl iodides and 1-bromo-2-naphthol.
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