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

Katharina Rode; Martina Palomba; Stefan Ortgies; Rene Rieger; Alexander Breder

doi:10.1055/s-0037-1609938

Synthesis, Table of Contents

Synthesis 2018; 50(19): 3875-3885
DOI: 10.1055/s-0037-1609938

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

Katharina Rode

^aInstitut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany Email: abreder@gwdg.de

,

Martina Palomba

^bDepartment of Pharmaceutical Sciences, Faculty of Pharmacy, University of Perugia, Via Fabretti, 48 - 06123 Perugia, Italy

,

Stefan Ortgies

^aInstitut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany Email: abreder@gwdg.de

,

Rene Rieger

^aInstitut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany Email: abreder@gwdg.de

,

Alexander Breder *

^aInstitut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany Email: abreder@gwdg.de

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Abstract

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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.

Key words

alcohols - allylations - alkenes - oxidations - photoredox catalysis - selenium-π-acids

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References

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