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Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds by a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction.
Org Lett. 2018 12 07; 20(23):7731-7734.OL

Abstract

A highly chemoselective intermolecular annulation reaction of phenol-based biaryls with bromoalkyl alkynes has been successfully developed by palladium/norbornene catalysis. This domino process was accomplished by following a cascade of Catellani-type C-H functionalization, alkyne migratory insertion, and arene dearomatization, thus leading to a large number of spiro[4,5]decane-embedded polycyclic molecules bearing various functional groups in moderate to excellent yields.

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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 710069 , China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science , Northwest University , Xi'an 710069 , China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science , Northwest University , Xi'an 710069 , China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science , Northwest University , Xi'an 710069 , China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science , Northwest University , Xi'an 710069 , China.

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

30489091

Citation

Nan, Jiang, et al. "Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds By a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction." Organic Letters, vol. 20, no. 23, 2018, pp. 7731-7734.

Nan J, Yuan Y, Bai L, et al. Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds by a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction. Org Lett. 2018;20(23):7731-7734.

Nan, J., Yuan, Y., Bai, L., Liu, J., & Luan, X. (2018). Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds by a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction. Organic Letters, 20(23), 7731-7734. https://doi.org/10.1021/acs.orglett.8b03518

Nan J, et al. Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds By a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction. Org Lett. 2018 12 7;20(23):7731-7734. PubMed PMID: 30489091.

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

TY - JOUR T1 - Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds by a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction. AU - Nan,Jiang, AU - Yuan,Yini, AU - Bai,Lu, AU - Liu,Jingjing, AU - Luan,Xinjun, Y1 - 2018/11/29/ PY - 2018/11/30/pubmed PY - 2018/11/30/medline PY - 2018/11/30/entrez SP - 7731 EP - 7734 JF - Organic letters JO - Org Lett VL - 20 IS - 23 N2 - A highly chemoselective intermolecular annulation reaction of phenol-based biaryls with bromoalkyl alkynes has been successfully developed by palladium/norbornene catalysis. This domino process was accomplished by following a cascade of Catellani-type C-H functionalization, alkyne migratory insertion, and arene dearomatization, thus leading to a large number of spiro[4,5]decane-embedded polycyclic molecules bearing various functional groups in moderate to excellent yields. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/30489091/Highly_Chemoselective_Construction_of_Spiro[45]decane_Embedded_Polycyclic_Scaffolds_by_a_Palladium/Norbornene_Catalyzed_C_H_Activation/Arene_Dearomatization_Reaction_ DB - PRIME DP - Unbound Medicine ER -