Superbase‐Promoted Addition of Acetylene Gas to the C=N Bond
Реакция присоединения ацетилена к двойной связи C=N, инициируемая сверхосновой
2019-08-13
SCID: 54.1/jbkfvtxj
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C=N bond additionCsp3–Csp bond formationacetylene gassuperbase KOtBu/DMSOα‑aminoacetylenes
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Abstract (AI)
A new Csp 3 –Csp bond forming reaction is reported: the C=N bond of widespread imines reacts with acetylene gas in the presence of superbase KO t Bu/DMSO at room temperature to afford terminal α‐aminoacetylenes in up to 94 % yield. The reaction allows nitrogen heterocycles, e.g. 3H‐indoles, to be directly cross‐coupled with acetylene gas.
Key Findings
1
A new Csp3–Csp bond-forming reaction was developed: imine C=N bonds react with acetylene gas to give α-aminoacetylenes.
2
Terminal α-aminoacetylenes are obtained in yields up to 94%.
3
The method enables direct cross-coupling of nitrogen heterocycles, such as 3H-indoles, with acetylene gas.
4
The transformation uses superbase KOtBu in DMSO at room temperature.
Research Object
Imines (C=N bonds) undergoing addition of acetylene gas promoted by superbase KOtBu/DMSO
Research Subject
Formation of Csp3–Csp bonds yielding terminal α‑aminoacetylenes via superbase‑promoted addition of acetylene to imine C=N bonds, including direct cross‑coupling of nitrogen heterocycles (e.g., 3H‑indoles) with acetylene gas and associated yields
Publication Details
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2019-08-13
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