Topic
Acetonitrile
About: Acetonitrile is a research topic. Over the lifetime, 11298 publications have been published within this topic receiving 175275 citations. The topic is also known as: cyanomethane & ethyl nitrile.
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TL;DR: A sequence involving the copper-mediated generation of a cyanomethyl radical and its subsequent addition to an alkene, and a C(sp3 )-N bond formation accounted for the reaction outcome.
Abstract: A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded γ-azido alkyl nitriles by formation of one C(sp3 )-C(sp3 ) bond and one C(sp3 )-N bond. The transformation allows concomitant introduction of two highly versatile groups (CN and N3 ) across the double bond. A sequence involving the copper-mediated generation of a cyanomethyl radical and its subsequent addition to an alkene, and a C(sp3 )-N bond formation accounted for the reaction outcome. The resulting γ-azido alkyl nitrile can be easily converted into 1,4-diamines, γ-amino nitriles, γ-azido esters, and γ-lactams of significant synthetic value.
111 citations
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TL;DR: A copper-mediated C2-cyanation of indoles using cheap and commercially available acetonitrile as the "nonmetallic" cyanide source was achieved through sequential C-C and C-H bond cleavages, providing a novel and alternative route leading to indole-2-carbonitrile.
Abstract: A copper-mediated C2-cyanation of indoles using cheap and commercially available acetonitrile as the “nonmetallic” cyanide source was achieved through sequential C–C and C–H bond cleavages. The installation of a removable pyrimidyl group on the indole nitrogen atom is the key for this C2 selectivity. This approach provides a novel and alternative route leading to indole-2-carbonitrile.
111 citations
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TL;DR: In this paper, it was shown that cyclotriborazane and borazine can be formed in 0.15 M NH3BH3 in diglyme at 130 °C.
110 citations
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TL;DR: In this paper, anhydrous Chloramine-T was added to an acetonitrile solution of alkenes in the presence of various CuCl catalysts and MS-5A, and the corresponding aziridines were obtained in moderate to good yields.
110 citations
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TL;DR: It is suggested that methanol be used as the preferred organic modifier with phenyl columns to achieve selectivity based upon pi-pi interactions.
109 citations