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Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.
Chem Sci. 2015 Feb 01; 6(2):1265-1271.CS

Abstract

The generation of gold carbenes via the gold-catalyzed intermolecular reaction of nucleophiles containing relatively labile N-O or N-N bonds with alkynes has received considerable attention during recent years. However, this protocol is not atom-economic as the reaction produces a stoichiometric amount of pyridine or quinoline waste, the cleaved part of the N-O or N-N bonds. In this article, we disclose an unprecedented gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles, allowing rapid and practical access to a wide range of synthetically-useful 2-aminopyrroles. Most importantly, mechanistic studies and theoretical calculations revealed that this reaction presumably proceeds via an α-imino gold carbene pathway, thus providing a strategically novel, atom-economic route to the generation of gold carbenes. Other significant features of this approach include the use of readily-available starting materials, high flexibility, simple procedure, mild reaction conditions, and in particular, no need to exclude moisture or air ("open flask").

Authors+Show Affiliations

State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Theoretical and Computational Chemistry of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen , 361005 , Fujian , P. R. China . Email: xinlu@xmu.edu.cn.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.State Key Laboratory of Physical Chemistry of Solid Surfaces , Key Laboratory for Theoretical and Computational Chemistry of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen , 361005 , Fujian , P. R. China . Email: xinlu@xmu.edu.cn.State Key Laboratory for Physical Chemistry of Solid Surfaces , The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry , College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , Fujian , P. R. China . Email: longwuye@xmu.edu.cn ; ; Tel: +86-592-218-5833.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29560212

Citation

Zhou, Ai-Hua, et al. "Atom-economic Generation of Gold Carbenes: Gold-catalyzed Formal [3+2] Cycloaddition Between Ynamides and Isoxazoles." Chemical Science, vol. 6, no. 2, 2015, pp. 1265-1271.
Zhou AH, He Q, Shu C, et al. Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles. Chem Sci. 2015;6(2):1265-1271.
Zhou, A. H., He, Q., Shu, C., Yu, Y. F., Liu, S., Zhao, T., Zhang, W., Lu, X., & Ye, L. W. (2015). Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles. Chemical Science, 6(2), 1265-1271. https://doi.org/10.1039/c4sc02596b
Zhou AH, et al. Atom-economic Generation of Gold Carbenes: Gold-catalyzed Formal [3+2] Cycloaddition Between Ynamides and Isoxazoles. Chem Sci. 2015 Feb 1;6(2):1265-1271. PubMed PMID: 29560212.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles. AU - Zhou,Ai-Hua, AU - He,Qiao, AU - Shu,Chao, AU - Yu,Yong-Fei, AU - Liu,Shuang, AU - Zhao,Tian, AU - Zhang,Wei, AU - Lu,Xin, AU - Ye,Long-Wu, Y1 - 2014/11/12/ PY - 2014/08/26/received PY - 2014/11/12/accepted PY - 2018/3/22/entrez PY - 2015/2/1/pubmed PY - 2015/2/1/medline SP - 1265 EP - 1271 JF - Chemical science JO - Chem Sci VL - 6 IS - 2 N2 - The generation of gold carbenes via the gold-catalyzed intermolecular reaction of nucleophiles containing relatively labile N-O or N-N bonds with alkynes has received considerable attention during recent years. However, this protocol is not atom-economic as the reaction produces a stoichiometric amount of pyridine or quinoline waste, the cleaved part of the N-O or N-N bonds. In this article, we disclose an unprecedented gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles, allowing rapid and practical access to a wide range of synthetically-useful 2-aminopyrroles. Most importantly, mechanistic studies and theoretical calculations revealed that this reaction presumably proceeds via an α-imino gold carbene pathway, thus providing a strategically novel, atom-economic route to the generation of gold carbenes. Other significant features of this approach include the use of readily-available starting materials, high flexibility, simple procedure, mild reaction conditions, and in particular, no need to exclude moisture or air ("open flask"). SN - 2041-6520 UR - https://www.unboundmedicine.com/medline/citation/29560212/Atom_economic_generation_of_gold_carbenes:_gold_catalyzed_formal_[3+2]_cycloaddition_between_ynamides_and_isoxazoles_ L2 - https://doi.org/10.1039/c4sc02596b DB - PRIME DP - Unbound Medicine ER -
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