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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.ORCID iD: 0000-0002-1333-7740
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-7898-317X
2015 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 2, p. 708-714Article 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, p. 708-714
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, id: 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: 2018-03-26Bibliographically approved

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Vazquez-Romero, AnaBermejo Gómez, AntonioMartín-Matute, Belén
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