Synthesis 2018; 50(19): 3875-3885
DOI: 10.1055/s-0037-1609938
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© Georg Thieme Verlag Stuttgart · New York

Aerobic Allylation of Alcohols with Non-Activated Alkenes Enabled by Light-Driven Selenium-π-Acid Catalysis

Katharina Rode
a  Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany   Email: abreder@gwdg.de
,
Martina Palomba
b  Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Perugia, Via Fabretti, 48 - 06123 Perugia, Italy
,
Stefan Ortgies
a  Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany   Email: abreder@gwdg.de
,
Rene Rieger
a  Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany   Email: abreder@gwdg.de
,
a  Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany   Email: abreder@gwdg.de
› Author Affiliations
This work was financially supported by the German Research Foundation [DFG, Emmy Noether Fellowship to A.B. (BR-4907/1-1)], the Lower Saxony Ministry for Science and Culture (Georg-Christoph-Lichtenberg Fellowship to K.R.), and the Fonds der Chemischen Industrie (Ph.D. Fellowship to S.O.).
Further Information

Publication History

Received: 05 June 2018

Accepted after revision: 06 August 2018

Publication Date:
23 August 2018 (online)

Abstract

A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photo­redox catalyst by means of a light-induced electron transfer process. Under optimized conditions, a broad range of both cyclic and acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity.

Supporting Information

 
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