Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect.
J Org Chem. 2021 07 16; 86(14):9711-9722.JO

Abstract

The efficient couplings of diverse N-arylureas and gem-difluoromethylene alkynes have been realized via Rh(III)-catalyzed chemoselective C-H alkenylation and [5 + 1] annulation, which were induced by the distinctive fluorine effect to provide the different coordination mode of the Rh(III) catalyst binding to the directing group, thereby giving the direct access to difluorinated 2-alkenyl arylureas and 3,4-dihydroquinazolin-2(1H)-ones bearing both an α-quaternary carbon center and a monofluoroalkenyl moiety with broad substrate compatibility and good functional group tolerance. The synthetic application in C-H alkenylation of the N-pyridylaniline, the late-stage [3 + 2] annulation, and the derivation of the obtained products has been also demonstrated to further strengthen the synthetic utility of the chemodivergent transformations.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang J

Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, P. R. China.

MeSH

AlkynesCarbonCatalysisFluorineRhodium

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

34189921

Citation

Yang, Jian, et al. "Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation With Gem-Difluoromethylene Enabled By the Distinctive Fluorine Effect." The Journal of Organic Chemistry, vol. 86, no. 14, 2021, pp. 9711-9722.

Yang J, Shi W, Chen W, et al. Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect. J Org Chem. 2021;86(14):9711-9722.

Yang, J., Shi, W., Chen, W., Gao, H., Zhou, Z., & Yi, W. (2021). Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect. The Journal of Organic Chemistry, 86(14), 9711-9722. https://doi.org/10.1021/acs.joc.1c01012

Yang J, et al. Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation With Gem-Difluoromethylene Enabled By the Distinctive Fluorine Effect. J Org Chem. 2021 07 16;86(14):9711-9722. PubMed PMID: 34189921.

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

TY - JOUR T1 - Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect. AU - Yang,Jian, AU - Shi,Wendi, AU - Chen,Weijie, AU - Gao,Hui, AU - Zhou,Zhi, AU - Yi,Wei, Y1 - 2021/06/30/ PY - 2021/7/1/pubmed PY - 2021/8/7/medline PY - 2021/6/30/entrez SP - 9711 EP - 9722 JF - The Journal of organic chemistry JO - J Org Chem VL - 86 IS - 14 N2 - The efficient couplings of diverse N-arylureas and gem-difluoromethylene alkynes have been realized via Rh(III)-catalyzed chemoselective C-H alkenylation and [5 + 1] annulation, which were induced by the distinctive fluorine effect to provide the different coordination mode of the Rh(III) catalyst binding to the directing group, thereby giving the direct access to difluorinated 2-alkenyl arylureas and 3,4-dihydroquinazolin-2(1H)-ones bearing both an α-quaternary carbon center and a monofluoroalkenyl moiety with broad substrate compatibility and good functional group tolerance. The synthetic application in C-H alkenylation of the N-pyridylaniline, the late-stage [3 + 2] annulation, and the derivation of the obtained products has been also demonstrated to further strengthen the synthetic utility of the chemodivergent transformations. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/34189921/Rh_III__Catalyzed_Chemoselective_C_H_Alkenylation_and_[5_+_1]_Annulation_with_Gem_Difluoromethylene_Enabled_by_the_Distinctive_Fluorine_Effect_ DB - PRIME DP - Unbound Medicine ER -

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Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect.J Org Chem. 2021 07 16; 86(14):9711-9722.JO