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Ru(II)-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach.
J Am Chem Soc. 2013 Nov 20; 135(46):17306-9.JA

Abstract

Intermolecular annulation reactions of 1-aryl-2-naphthols with internal alkynes proceed efficiently in the presence of a Ru catalyst and a Cu oxidant to generate spirocyclic compounds by sequential cleavage of the C(sp(2))-H bond, migratory insertion of the alkyne, and dearomatization of the naphthyl ring. Various spirocyclic molecules bearing an all-carbon quaternary stereocenter could be obtained by this novel method with good yields and excellent regioselectivity, and the current process tolerates a variety of synthetically important functional groups.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nan J
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710069, China.
Zuo Z
No affiliation info available
Luo L
No affiliation info available
Bai L
No affiliation info available
Zheng H
No affiliation info available
Yuan Y
No affiliation info available
Liu J
No affiliation info available
Luan X
No affiliation info available
Wang Y
No affiliation info available

MeSH

AlkynesCatalysisCyclizationMolecular StructureNaphtholsRutheniumSpiro Compounds

Pub Type(s)

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

Language

eng

PubMed ID

24195654

Citation

Nan, Jiang, et al. "Ru(II)-catalyzed Vinylative Dearomatization of Naphthols Via a C(sp2)-H Bond Activation Approach." Journal of the American Chemical Society, vol. 135, no. 46, 2013, pp. 17306-9.
Nan J, Zuo Z, Luo L, et al. Ru(II)-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach. J Am Chem Soc. 2013;135(46):17306-9.
Nan, J., Zuo, Z., Luo, L., Bai, L., Zheng, H., Yuan, Y., Liu, J., Luan, X., & Wang, Y. (2013). Ru(II)-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach. Journal of the American Chemical Society, 135(46), 17306-9. https://doi.org/10.1021/ja410060e
Nan J, et al. Ru(II)-catalyzed Vinylative Dearomatization of Naphthols Via a C(sp2)-H Bond Activation Approach. J Am Chem Soc. 2013 Nov 20;135(46):17306-9. PubMed PMID: 24195654.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ru(II)-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach. AU - Nan,Jiang, AU - Zuo,Zhijun, AU - Luo,Lei, AU - Bai,Lu, AU - Zheng,Huayu, AU - Yuan,Yini, AU - Liu,Jingjing, AU - Luan,Xinjun, AU - Wang,Yaoyu, Y1 - 2013/11/06/ PY - 2013/11/8/entrez PY - 2013/11/8/pubmed PY - 2014/7/6/medline SP - 17306 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 135 IS - 46 N2 - Intermolecular annulation reactions of 1-aryl-2-naphthols with internal alkynes proceed efficiently in the presence of a Ru catalyst and a Cu oxidant to generate spirocyclic compounds by sequential cleavage of the C(sp(2))-H bond, migratory insertion of the alkyne, and dearomatization of the naphthyl ring. Various spirocyclic molecules bearing an all-carbon quaternary stereocenter could be obtained by this novel method with good yields and excellent regioselectivity, and the current process tolerates a variety of synthetically important functional groups. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/24195654/Ru_II__catalyzed_vinylative_dearomatization_of_naphthols_via_a_C_sp2__H_bond_activation_approach_ DB - PRIME DP - Unbound Medicine ER -