Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands with 
Restricted Flexibility for Catalysis

Altenhoff, Gereon; Goddard, Richard; Lehmann, Christian W.; Glorius, Frank

doi:10.1021/ja045349r

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Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands with Restricted Flexibility for Catalysis

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Altenhoff, Gereon
Research Group Glorius, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard, Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann, Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Glorius, Frank
Research Group Glorius, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Altenhoff, G., Goddard, R., Lehmann, C. W., & Glorius, F. (2004). Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands with Restricted Flexibility for Catalysis. Journal of the American Chemical Society, 126(46), 15195-15201. doi:10.1021/ja045349r.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9743-6

Abstract

A unique family of N-heterocyclic carbenes derived from bioxazolines (IBiox) suitable for application in transition-metal catalysis is described. The ligands are electron rich, sterically demanding, and have restricted flexibility. Their usefulness has been demonstrated in the Suzuki−Miyaura cross-coupling of sterically hindered aryl chlorides and boronic acids. For the first time, tetraortho-substituted biaryls with methyl and larger ortho-substituents have been synthesized from aryl chlorides using the Suzuki−Miyaura method.