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...
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| Published in | Tetrahedron letters Vol. 61; no. 39; pp. 152374 - 152377 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
24.09.2020
Elsevier |
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| Abstract | [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. |
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| AbstractList | [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. 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 degrees-propargyl alcohols and a subsequent 1,2-shift lead to the formation of beta-iodo-alpha,beta-unsaturated cyclic and acyclic ketones in good yields. In the case of cyclic ketones, the products are obtained with ring expansion. (C) 2020 Elsevier Ltd. All rights reserved. |
| ArticleNumber | 152374 |
| Author | Mahesh Kumar, K. Almansour, Abdulrahman I. Arumugam, Natarajan Yaragorla, Srinivasarao Khan, Tabassum |
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| Cites_doi | 10.1021/jo020457m 10.1021/ol203375y 10.1002/ejoc.201001479 10.1021/ol901346k 10.1002/ejoc.201901393 10.1021/jo0503310 10.1021/ol502224s 10.1039/c6cs00935b 10.1021/ja202959n 10.1021/ja060282o 10.1002/cssc.201900784 10.1055/s-2005-868495 10.1016/j.tetlet.2007.10.055 10.1021/ja0466964 10.1007/s11164-012-0765-9 10.1021/ja503944n 10.1021/ol034745w 10.1021/acsomega.8b02393 10.1055/s-2004-831214 10.1002/ejoc.201800248 10.1002/slct.201601349 10.1002/ajoc.201800089 10.1039/c5qo00048c 10.1002/ejoc.201900474 10.1021/jo070230x 10.1039/b912099h 10.1002/ejoc.201700668 10.1021/jo202241b 10.1080/00397919708004113 10.1016/S0040-4039(99)00635-8 10.1039/C6CS00935B 10.1021/ja01465a034 10.15227/orgsyn.046.0089 10.1002/1521-3773(20020315)41:6<996::AID-ANIE996>3.0.CO;2-I 10.1021/ja0002823 10.1021/cr60240a003 10.1016/S0040-4020(01)01228-5 10.1016/S0040-4039(00)98353-9 10.1039/C5QO00048C 10.1021/cr60273a001 10.1016/S0040-4039(00)79328-2 10.1021/ja01076a089 10.1016/S0040-4039(00)91094-3 10.1016/S0040-4039(00)91575-2 |
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| Issue | 39 |
| Keywords | 1,2-Migration Propargyl alcohols Ketones Alkynes Ring expansion MEYER-SCHUSTER REARRANGEMENT METHYL MIGRATION IODOCYCLIZATION INDOLES CYCLOISOMERIZATION ALPHA-IODINATION CYCLIZATION HIGHLY SUBSTITUTED FURANS |
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•Cyclocarbonylation-iodination of arynes.•Ring expansion.•1,2-migration.•One-Pot, three-component, room temperature reaction.•Good yields and... A simple, three-component, one-pot, room-temperature reaction of cyclocarbonylation-iodination is developed from terminal alkynes, ketones, and ICl. The... |
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| SubjectTerms | 1,2-Migration Alkynes Chemistry Chemistry, Organic Ketones Physical Sciences Propargyl alcohols Ring expansion Science & Technology |
| Title | Cyclocarbonylation-Iodination of terminal alkynes with ketones and ICl via 1,2-migration |
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