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Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization.
Angew Chem Int Ed Engl. 2019 01 28; 58(5):1474-1478.AC

Abstract

A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp3)-H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation-facilitated C(sp3)-H activation, biaryl cross-coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional-group tolerance. Preliminary mechanistic studies indicate that C-H cleavage is likely involved in the rate-determining step, and a five-membered palladacycle was identified as the key intermediate for the intermolecular coupling.

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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

30537202

Citation

Tan, Bojun, et al. "Palladium-Catalyzed Intermolecular [4+1] Spiroannulation By C(sp3)-H Activation and Naphthol Dearomatization." Angewandte Chemie (International Ed. in English), vol. 58, no. 5, 2019, pp. 1474-1478.

Tan B, Bai L, Ding P, et al. Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization. Angew Chem Int Ed Engl. 2019;58(5):1474-1478.

Tan, B., Bai, L., Ding, P., Liu, J., Wang, Y., & Luan, X. (2019). Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization. Angewandte Chemie (International Ed. in English), 58(5), 1474-1478. https://doi.org/10.1002/anie.201813202

Tan B, et al. Palladium-Catalyzed Intermolecular [4+1] Spiroannulation By C(sp3)-H Activation and Naphthol Dearomatization. Angew Chem Int Ed Engl. 2019 01 28;58(5):1474-1478. PubMed PMID: 30537202.

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

TY - JOUR T1 - Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3)-H Activation and Naphthol Dearomatization. AU - Tan,Bojun, AU - Bai,Lu, AU - Ding,Pin, AU - Liu,Jingjing, AU - Wang,Yaoyu, AU - Luan,Xinjun, Y1 - 2019/01/03/ PY - 2018/11/19/received PY - 2018/12/12/pubmed PY - 2018/12/12/medline PY - 2018/12/12/entrez KW - C−H activation KW - cyclization KW - dearomatization KW - palladium KW - spiro compounds SP - 1474 EP - 1478 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 5 N2 - A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp3)-H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation-facilitated C(sp3)-H activation, biaryl cross-coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional-group tolerance. Preliminary mechanistic studies indicate that C-H cleavage is likely involved in the rate-determining step, and a five-membered palladacycle was identified as the key intermediate for the intermolecular coupling. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30537202/Palladium_Catalyzed_Intermolecular_[4+1]_Spiroannulation_by_C_sp3__H_Activation_and_Naphthol_Dearomatization_ DB - PRIME DP - Unbound Medicine ER -