Aldimines react with aryl- and hetarylacetylenes in the presence of KOBu/dimethyl sulfoxide (DMSO) or NaOBu/DMSO systems under exceptionally mild conditions (14 °C, 1 h) to afford C-H-vinylated products, 1-azadienes of 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-Csp bond-forming reaction opens a straightforward pot-, atom-, step-, and energy-economic access to synthetically valuable 1-azadienes.
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Transition-Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines with Acetylenes to 1-Azadienes.
J Org Chem
March 2020
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russian Federation.
Aldimines react with aryl- and hetarylacetylenes in the presence of KOBu/dimethyl sulfoxide (DMSO) or NaOBu/DMSO systems under exceptionally mild conditions (14 °C, 1 h) to afford C-H-vinylated products, 1-azadienes of 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-Csp bond-forming reaction opens a straightforward pot-, atom-, step-, and energy-economic access to synthetically valuable 1-azadienes.
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