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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.

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 710069, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

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_ L2 - https://doi.org/10.1021/ja410060e DB - PRIME DP - Unbound Medicine ER -