Transition-Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines with Acetylenes to 1-Azadienes

被引：21

作者：

Schmidt, Elena Yu. ^{[1
]}

Bidusenko, Ivan A. ^{[1
]}

Protsuk, Nadezhda I. ^{[1
]}

Demyanov, Yan V. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Vashchenko, Alexander V. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

ALPHA; BETA-UNSATURATED IMINES; SYNTHETIC APPLICATIONS; EFFICIENT SYNTHESIS; STEP ECONOMY; POT; ALDEHYDES; REDUCTION; KETONES; AMINES; ATOM;

D O I：

10.1021/acs.joc.9b03192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldimines react with aryl- and hetarylacetylenes in the presence of KOBut/dimethyl sulfoxide (DMSO) or NaOBut/DMSO systems under exceptionally mild conditions (14 degrees C, 1 h) to afford C-H-vinylated products, 1-azadienes of E configuration relative to the C-C bond, in up to 72% yield. Vinylation involves the unprecedentedly fast multiposition proton transfer in the intermediate adducts of acetylene to the C=N bond. This new Csp(2)-Csp(2) bond-forming reaction opens a straightforward pot-, atom-, step-, and energy-economic access to synthetically valuable 1-azadienes.

引用

页码：3417 / 3425

页数：9

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