C-C Bond Activation pp 85-110

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 346) | Cite as

Carbon–Carbon Bond Activation with 8-Acylquinolines

Chapter

Abstract

Synthetically relevant advances in the area of carbon–carbon sigma bond activation have been made possible by 8-acylquinoline directing groups. Stable rhodium metallacycle intermediates have been shown to undergo a variety of transformations, including carboacylation reactions, to produce value-added products containing all-carbon quaternary centers. The kinetic profile of such reactions has been shown to be substrate dependent.

Keywords

8-Acylquinoline 8-Quinolinyl ketone All-carbon quaternary centers Bond insertion Carboacylation Carbon–carbon bond activation Chelation Cyclometalation Directed metalation Directing group Metallacycle Oxidative addition Rhodium catalyst 

Abbreviations

BDE

Bond dissociation energy

brsm

Based on recovered starting material

C–C

Carbon–carbon sigma bond

C–CN

Carbon–nitrile bond

C–H

Carbon–hydrogen bond

cod

Cyclooctadiene

MeCN

Acetonitrile

OAc

Acetate

PhMe

Toluene

py

Pyridine

THF

Tetrahydrofuran

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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of MinnesotaMinneapolisUSA

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