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

[Display omitted] •Cyclocarbonylation-iodination of arynes.•Ring expansion.•1,2-migration.•One-Pot, three-component, room temperature reaction.•Good yields and Substrate scope. A simple, three-component, one-pot, room-temperature reaction of cyclocarbonylation-iodination is developed from terminal a...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 61; no. 39; pp. 152374 - 152377
Main Authors Mahesh Kumar, K., Khan, Tabassum, Almansour, Abdulrahman I., Arumugam, Natarajan, Yaragorla, Srinivasarao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.09.2020
Elsevier
Subjects
1,2-Migration
Alkynes
Chemistry
Chemistry, Organic
Ketones
Physical Sciences
Propargyl alcohols
Ring expansion
Science & Technology
1,2-Migration
Propargyl alcohols
Ketones
Alkynes
Ring expansion
MEYER-SCHUSTER REARRANGEMENT
METHYL MIGRATION
IODOCYCLIZATION
INDOLES
CYCLOISOMERIZATION
ALPHA-IODINATION
CYCLIZATION
HIGHLY SUBSTITUTED FURANS
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] •Cyclocarbonylation-iodination of arynes.•Ring expansion.•1,2-migration.•One-Pot, three-component, room temperature reaction.•Good yields and Substrate scope. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152374