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Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides with Alkynes.
Org Lett. 2021 Jun 16 [Online ahead of print]OL

Abstract

Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34132559

Citation

Liao, Xingrong, et al. "Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides With Alkynes." Organic Letters, 2021.

Liao X, Zhou F, Bin Z, et al. Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides with Alkynes. Org Lett. 2021.

Liao, X., Zhou, F., Bin, Z., Yang, Y., & You, J. (2021). Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides with Alkynes. Organic Letters. https://doi.org/10.1021/acs.orglett.1c01736

Liao X, et al. Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides With Alkynes. Org Lett. 2021 Jun 16; PubMed PMID: 34132559.

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

TY - JOUR T1 - Palladium-Catalyzed Cascade Dearomative Spirocyclization and C-H Annulation of Aromatic Halides with Alkynes. AU - Liao,Xingrong, AU - Zhou,Fulin, AU - Bin,Zhengyang, AU - Yang,Yudong, AU - You,Jingsong, Y1 - 2021/06/16/ PY - 2021/6/16/entrez PY - 2021/6/17/pubmed PY - 2021/6/17/medline JF - Organic letters JO - Org Lett N2 - Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/34132559/Palladium_Catalyzed_Cascade_Dearomative_Spirocyclization_and_C_H_Annulation_of_Aromatic_Halides_with_Alkynes_ DB - PRIME DP - Unbound Medicine ER -