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Cyclocarbonylation-Iodination of terminal alkynes with ketones and ICl via 1,2-migration

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Abstract A simple, three-component, one-pot, room-temperature reaction of cyclocarbonylation-iodination is developed from terminal alkynes, ketones, and ICl. The reaction proceeds through the formation of 3°-propargyl alcohols and a subsequent 1,2-shift… Click to show full abstract

Abstract A simple, three-component, one-pot, room-temperature reaction of cyclocarbonylation-iodination is developed from terminal alkynes, ketones, and ICl. The reaction proceeds through the formation of 3°-propargyl alcohols and a subsequent 1,2-shift lead to the formation of β-iodo-α,β-unsaturated cyclic and acyclic ketones in good yields. In the case of cyclic ketones, the products are obtained with ring expansion.

Keywords: ketones icl; alkynes ketones; cyclocarbonylation iodination; iodination terminal; terminal alkynes

Journal Title: Tetrahedron Letters
Year Published: 2020

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