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Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks.
Angew Chem Int Ed Engl. 2018 04 23; 57(18):5151-5155.AC

Abstract

Reported is a highly chemoselective intermolecular annulation of indole-based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani-type C-H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp2)-C(sp3) and one C(sp2)-C(sp2) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment, in good yields with excellent functional-group tolerance. Preliminary mechanistic studies reveal that C-H bond cleavage is likely involved in the rate-determining step, and the indole dearomatization might take place through an olefin coordination/insertion and β-hydride elimination Heck-type pathway.

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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

29509316

Citation

Bai, Lu, et al. "Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks." Angewandte Chemie (International Ed. in English), vol. 57, no. 18, 2018, pp. 5151-5155.

Bai L, Liu J, Hu W, et al. Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks. Angew Chem Int Ed Engl. 2018;57(18):5151-5155.

Bai, L., Liu, J., Hu, W., Li, K., Wang, Y., & Luan, X. (2018). Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks. Angewandte Chemie (International Ed. in English), 57(18), 5151-5155. https://doi.org/10.1002/anie.201801894

Bai L, et al. Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks. Angew Chem Int Ed Engl. 2018 04 23;57(18):5151-5155. PubMed PMID: 29509316.

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

TY - JOUR T1 - Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks. AU - Bai,Lu, AU - Liu,Jingjing, AU - Hu,Wenjie, AU - Li,Kunyu, AU - Wang,Yaoyu, AU - Luan,Xinjun, Y1 - 2018/03/23/ PY - 2018/02/12/received PY - 2018/3/7/pubmed PY - 2018/3/7/medline PY - 2018/3/7/entrez KW - C−H activation KW - cyclizations KW - dearomatization KW - heterocycles KW - palladium SP - 5151 EP - 5155 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 57 IS - 18 N2 - Reported is a highly chemoselective intermolecular annulation of indole-based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani-type C-H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp2)-C(sp3) and one C(sp2)-C(sp2) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment, in good yields with excellent functional-group tolerance. Preliminary mechanistic studies reveal that C-H bond cleavage is likely involved in the rate-determining step, and the indole dearomatization might take place through an olefin coordination/insertion and β-hydride elimination Heck-type pathway. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/29509316/Palladium/Norbornene_Catalyzed_C_H_Alkylation/Alkyne_Insertion/Indole_Dearomatization_Domino_Reaction:_Assembly_of_Spiroindolenine_Containing_Pentacyclic_Frameworks_ DB - PRIME DP - Unbound Medicine ER -