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Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction.
Angew Chem Int Ed Engl. 2017 11 06; 56(45):14257-14261.AC

Abstract

A novel palladium-catalyzed three-component reaction of phenol-derived biaryls with N-benzoyloxyamines and norbornadiene (NBD) has been developed for the assembly of highly functionalized spiroindenes. This domino process was realized through NBD-assisted C-H amination and phenol dearomatization by forming one C-N bond and two C-C bonds in a single step. Preliminary studies indicated that asymmetric control of this transformation was feasible with chiral ligands. Moreover, the potential synthetic utility of this methodology was highlighted by a series of further transformations.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fan L
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.
Liu J
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.
Bai L
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.
Wang Y
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.
Luan X
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

28940876

Citation

Fan, Liangxin, et al. "Rapid Assembly of Diversely Functionalized Spiroindenes By a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction." Angewandte Chemie (International Ed. in English), vol. 56, no. 45, 2017, pp. 14257-14261.
Fan L, Liu J, Bai L, et al. Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction. Angew Chem Int Ed Engl. 2017;56(45):14257-14261.
Fan, L., Liu, J., Bai, L., Wang, Y., & Luan, X. (2017). Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction. Angewandte Chemie (International Ed. in English), 56(45), 14257-14261. https://doi.org/10.1002/anie.201708310
Fan L, et al. Rapid Assembly of Diversely Functionalized Spiroindenes By a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction. Angew Chem Int Ed Engl. 2017 11 6;56(45):14257-14261. PubMed PMID: 28940876.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction. AU - Fan,Liangxin, AU - Liu,Jingjing, AU - Bai,Lu, AU - Wang,Yaoyu, AU - Luan,Xinjun, Y1 - 2017/10/04/ PY - 2017/08/12/received PY - 2017/9/25/pubmed PY - 2017/9/25/medline PY - 2017/9/24/entrez KW - C−H amination KW - dearomatization KW - homogeneous catalysis KW - palladium KW - spiroannulation SP - 14257 EP - 14261 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 45 N2 - A novel palladium-catalyzed three-component reaction of phenol-derived biaryls with N-benzoyloxyamines and norbornadiene (NBD) has been developed for the assembly of highly functionalized spiroindenes. This domino process was realized through NBD-assisted C-H amination and phenol dearomatization by forming one C-N bond and two C-C bonds in a single step. Preliminary studies indicated that asymmetric control of this transformation was feasible with chiral ligands. Moreover, the potential synthetic utility of this methodology was highlighted by a series of further transformations. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28940876/Rapid_Assembly_of_Diversely_Functionalized_Spiroindenes_by_a_Three_Component_Palladium_Catalyzed_C_H_Amination/Phenol_Dearomatization_Domino_Reaction_ DB - PRIME DP - Unbound Medicine ER -