Ruthenium-Catalyzed Directed C(3)–H Olefination of N-Acetyl-1,2-dihydroisoquinolines: A Method to Achieve C3-Olefinated Isoquinolines

^§ Equal contribution

Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

A unique approach to achieve regioselective C(3)–H olefination of isoquinolines under ruthenium-catalyzed conditions has been developed. The acetyl group of N-acetyl-1,2-dihydroisoquinoline acts as a directing group for this C–H olefination strategy. Removal of the acetyl directing group by a simple method leads to a quick access to C-3 olefinated isoquinolines. The methodology is a very good alternative to the traditional Heck reaction and substrates with halogen substituents are very good candidates for the transformation.

Key words

ruthenium catalysis - C–H functionalization - isoquinolines - directing group - C–H olefination

• References

• 1 Present address: Department of Chemistry, University of Minnesota, 207 Pleasant Street S.E., Minneapolis, MN 55455-0431, USA.
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