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Updated: Mar 25, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Cobalt-Catalyzed [2+2+2] Cycloadditions of Alkynyl Yndiamides with Nitriles
Jun Fang1, William Parisot1, Phannarath Phansavath1
1PSL University, Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences, CSB2D Team, 75005 Paris, France.
Abstract:
Herein is described a convenient cobalt-catalyzed [2+2+2] cycloaddition of alkynyl yndiamides with nitriles. This regioselective reaction provides access to 39 novel valuable 2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-7-amine or (1,2,3,4-tetrahydro-1,7-naphthyridin-8-yl)-9H-carbazole derivatives. These highly substituted pyridines are important building blocks in medicinal chemistry. The process is eco-friendly since the cycloaddition is conducted in a green solvent with a non-noble transition metal catalyst.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.