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Acid- and Iridium-Catalyzed Tandem 1,3-Transposition/3,1-Hydrogen Shift/Chlorination of Allylic Alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2015 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 2, 708-714 p.Article in journal (Refereed) Published
Abstract [en]

A method for the selective synthesis of alpha-chlorocarbonyls from allylic alcohols is presented. The reaction occurs through an acid- and iridium-catalyzed tandem process that combines a 1,3-transposition, a 3,1-hydrogen shift, and a chlorination process, and can be applied to a wide range of alpha-aromatic and heteroaromatic secondary allylic alcohols. Saturated non-chlorinated ketones or other side-products derived from overchlorination were not detected.

Place, publisher, year, edition, pages
2015. Vol. 5, no 2, 708-714 p.
Keyword [en]
hydrogen transfer, chlorination, allylic alcohols, isomerization, iridium, 1, 3-transposition
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-115698DOI: 10.1021/cs501618hISI: 000349275300026OAI: oai:DiVA.org:su-115698DiVA: diva2:799258
Funder
Knut and Alice Wallenberg FoundationSwedish Research CouncilBerzelii Centre EXSELENT
Note

AuthorCount:3;

Available from: 2015-03-30 Created: 2015-03-27 Last updated: 2017-06-30Bibliographically approved

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Vazquez-Romero, AnaBermejo Gomez, AntonioMartin-Matute, Belén
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