Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions

Xixian Pan; Xiaolong Wan; Xin Yu; Hui Zhang; Weiqing Xie

doi:10.1055/s-0033-1338622

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(15): 2057-2064
DOI: 10.1055/s-0033-1338622

paper

Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions

Authors

Xixian Pan

^aDepartment of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Fax: +86(21)66134856 eMail: yehao7171@shu.edu.cn
Xiaolong Wan

^bSchool of Materials Science and Engineering, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China

^cState Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China Fax: +86(21)64166128 eMail: xiewq@mail.sioc.ac.cn
Xin Yu

^aDepartment of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Fax: +86(21)66134856 eMail: yehao7171@shu.edu.cn
Hui Zhang*

^aDepartment of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Fax: +86(21)66134856 eMail: yehao7171@shu.edu.cn
Weiqing Xie*

^cState Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China Fax: +86(21)64166128 eMail: xiewq@mail.sioc.ac.cn

Abstract

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Abstract

A decarboxylative hydroamination cascade reaction of 3-arylpropiolic acids with N-heterocycles under transition-metal-free conditions was developed. 3-Arylpropiolic acids were found to react smoothly with a range of N-heterocycles under the effect of t-BuOK to afford N-vinyl heterocycles in moderate to excellent yields. This reaction represents the first decarboxylative hydroamination of 3-arylpropiolic acids without the aid of a transition-metal catalyst.

Key words

alkynes - decarboxylation - hydroamination - N-vinyl heterocycle - potassium tert-butoxide

Volltext

Referenzen

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6 Extra-pure t-BuOK (sublimed grade, 99.99% trace metals basis) was purchased from Sigma–Aldrich.
7 Phenylacetylene was found to be labile in the presence of t-BuOK because no phenylacetylene was detected by GC under the same reaction conditions after 24 h.
8 No product was isolated when t-BuOK (2.2 equiv) was used, probably due to the instability of phenylacetylene in the presence of excess t-BuOK.

Zusatzmaterial

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