Using Rh(III)-catalyzed C-H activation as a tool for the selective functionalization of ketone-containing molecules

Mélissa Boultadakis-Arapinis; Matthew N Hopkinson; Frank Glorius

doi:10.1021/ol500258q

Using Rh(III)-catalyzed C-H activation as a tool for the selective functionalization of ketone-containing molecules

Org Lett. 2014 Mar 21;16(6):1630-3. doi: 10.1021/ol500258q. Epub 2014 Mar 3.

Authors

Mélissa Boultadakis-Arapinis¹, Matthew N Hopkinson, Frank Glorius

Affiliation

¹ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.

PMID: 24588566
DOI: 10.1021/ol500258q

Abstract

Due to the strong potential of C-H activation in many areas of organic chemistry, the use of a pre-existing carbonyl group for the installation of a directing group to enable selective and predictable α-alkenylation with activated olefins as coupling partners is described. This Heck-type reaction would then lead either to β,γ-unsaturated ketones or to variously substituted 1,4-butadienes depending on the conditions used for the cleavage of the directing group.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry
Butadienes / chemical synthesis*
Butadienes / chemistry
Catalysis
Ketones / chemistry*
Molecular Structure
Rhodium / chemistry*

Substances

Alkenes
Butadienes
Ketones
Rhodium