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Modular Assembly of Spirocarbocyclic Scaffolds through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes.
Angew Chem Int Ed Engl. 2017 03 01; 56(10):2767-2771.AC

Abstract

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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Publisher Full Text (DOI)

Authors+Show Affiliations

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.

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.

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.

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.

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.

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.

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

28128533

Citation

Zuo, Zhijun, et al. "Modular Assembly of Spirocarbocyclic Scaffolds Through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols With Aryl Iodides and Alkynes." Angewandte Chemie (International Ed. in English), vol. 56, no. 10, 2017, pp. 2767-2771.

Zuo Z, Wang H, Fan L, et al. Modular Assembly of Spirocarbocyclic Scaffolds through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes. Angew Chem Int Ed Engl. 2017;56(10):2767-2771.

Zuo, Z., Wang, H., Fan, L., Liu, J., Wang, Y., & Luan, X. (2017). Modular Assembly of Spirocarbocyclic Scaffolds through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes. Angewandte Chemie (International Ed. in English), 56(10), 2767-2771. https://doi.org/10.1002/anie.201612127

Zuo Z, et al. Modular Assembly of Spirocarbocyclic Scaffolds Through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols With Aryl Iodides and Alkynes. Angew Chem Int Ed Engl. 2017 03 1;56(10):2767-2771. PubMed PMID: 28128533.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Modular Assembly of Spirocarbocyclic Scaffolds through Pd0 -Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes. AU - Zuo,Zhijun, AU - Wang,Hui, AU - Fan,Liangxin, AU - Liu,Jingjing, AU - Wang,Yaoyu, AU - Luan,Xinjun, Y1 - 2017/01/27/ PY - 2016/12/14/received PY - 2017/1/28/pubmed PY - 2017/1/28/medline PY - 2017/1/28/entrez KW - C−H activation KW - dearomatization KW - homogeneous catalysis KW - palladium KW - spiroannulation SP - 2767 EP - 2771 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 10 N2 - 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. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28128533/Modular_Assembly_of_Spirocarbocyclic_Scaffolds_through_Pd0__Catalyzed_Intermolecular_Dearomatizing_[2+2+1]_Annulation_of_Bromonaphthols_with_Aryl_Iodides_and_Alkynes_ DB - PRIME DP - Unbound Medicine ER -