期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 17, 期 -, 页码 2417-2424出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.158
关键词
acetylene-oxadiazoles; Friedel-Crafts reaction; hydroarylation; superelectrophilic activation; triflic acid
资金
- Russian Foundation for Basic Research [20-03-00074 A]
Novel acetylene derivatives of 1,2,4-oxadiazoles were successfully synthesized and their reactivity towards arenes in triflic acid was studied.
Formation of E/Z-vinyl triflates from the acetylene bond of oxadiazoles was achieved, providing insights into the reaction mechanisms.
Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon-carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH to the acetylene bond of these oxadiazoles quantitatively resulted in E/Z-vinyl triflates. The reactions of the cationic intermediates have been studied by DFT calculations and the reaction mechanisms are discussed.
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