Copper-Catalyzed Alkenylation of Cyanamides

Antoine Nitelet, Johan Wouters, Damien F. Dewez, Gwilherm Evano

Research output: Contribution to journalArticle

Abstract

An efficient procedure for the copper-catalyzed cross-coupling between a broad range of cyanamides and iodoalkenes is reported. Upon reaction with catalytic amounts of copper(I) iodide and 2,2′-bisimidazole in the presence of cesium carbonate in DMF at 80 °C, a fast, regioselective, and stereoretentive cross-coupling occurs. This reaction, which was found to have a broad substrate scope, provides the first general entry to N-alkenylcyanamides, building blocks that hold great synthetic potential.

Original languageEnglish
Pages (from-to)6276-6279
Number of pages4
JournalOrganic Letters
Volume19
Issue number23
DOIs
Publication statusPublished - 1 Dec 2017

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Alkenylation
Cyanamide
cyanamides
cross coupling
Copper
copper
Substrates
entry
cesium
iodides
carbonates
cuprous iodide
cesium carbonate

Cite this

Nitelet, Antoine ; Wouters, Johan ; Dewez, Damien F. ; Evano, Gwilherm. / Copper-Catalyzed Alkenylation of Cyanamides. In: Organic Letters. 2017 ; Vol. 19, No. 23. pp. 6276-6279.
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Nitelet, A, Wouters, J, Dewez, DF & Evano, G 2017, 'Copper-Catalyzed Alkenylation of Cyanamides', Organic Letters, vol. 19, no. 23, pp. 6276-6279. https://doi.org/10.1021/acs.orglett.7b02859

Copper-Catalyzed Alkenylation of Cyanamides. / Nitelet, Antoine; Wouters, Johan; Dewez, Damien F.; Evano, Gwilherm.

In: Organic Letters, Vol. 19, No. 23, 01.12.2017, p. 6276-6279.

Research output: Contribution to journalArticle

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