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Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones.
J Org Chem. 2020 05 15; 85(10):6687-6696.JO

Abstract

A convenient method for the synthesis of aryl-functionalized spirocyclohexadienone scaffolds from alkyne-containing phenol-based biaryls with aryl halides via palladium-catalyzed cyclization/dearomatization/arylation is developed. The approach provides a series of spirocyclohexadienone molecules in moderate to high yields. The reaction occurs chemoselectively through dearomative C-arylation rather than common O-arylation of phenols.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Bai Y
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.
Liu A
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.
Wu XX
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.
Chen S
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.
Wang J
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

Pub Type(s)

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

Language

eng

PubMed ID

32345018

Citation

Bai, Yunlong, et al. "Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls With Aryl Halides: an Entry to Diversely Functionalized Spirocyclohexadienones." The Journal of Organic Chemistry, vol. 85, no. 10, 2020, pp. 6687-6696.
Bai Y, Liu A, Wu XX, et al. Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones. J Org Chem. 2020;85(10):6687-6696.
Bai, Y., Liu, A., Wu, X. X., Chen, S., & Wang, J. (2020). Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones. The Journal of Organic Chemistry, 85(10), 6687-6696. https://doi.org/10.1021/acs.joc.0c00710
Bai Y, et al. Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls With Aryl Halides: an Entry to Diversely Functionalized Spirocyclohexadienones. J Org Chem. 2020 05 15;85(10):6687-6696. PubMed PMID: 32345018.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones. AU - Bai,Yunlong, AU - Liu,Anjia, AU - Wu,Xin-Xing, AU - Chen,Shufeng, AU - Wang,Jianbo, Y1 - 2020/05/07/ PY - 2020/4/30/pubmed PY - 2020/4/30/medline PY - 2020/4/30/entrez SP - 6687 EP - 6696 JF - The Journal of organic chemistry JO - J Org Chem VL - 85 IS - 10 N2 - A convenient method for the synthesis of aryl-functionalized spirocyclohexadienone scaffolds from alkyne-containing phenol-based biaryls with aryl halides via palladium-catalyzed cyclization/dearomatization/arylation is developed. The approach provides a series of spirocyclohexadienone molecules in moderate to high yields. The reaction occurs chemoselectively through dearomative C-arylation rather than common O-arylation of phenols. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/32345018/Palladium_Catalyzed_Cascade_Cyclization/Dearomatization/Arylation_of_Alkyne_Containing_Phenol_Based_Biaryls_with_Aryl_Halides:_An_Entry_to_Diversely_Functionalized_Spirocyclohexadienones_ DB - PRIME DP - Unbound Medicine ER -
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