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Journal
Publications |
ortho,ortho’-Substituted KITPHOS Monophosphines: Highly
Efficient Ligands for Palladium-Catalyzed CC and CN Bond Formation.
Simon Doherty, Julian G.
Knight, John P. McGrady, Alexandra M. Ferguson, Nicholas A. B. Ward,
Ross W. Harrington, and William Clegg, Adv. Synth. Catal.,
2010,
352, 201. |
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Abstract:
ortho,ortho’-Substitution of
the phosphinoalkyne-derived aryl ring in KITPHOS
(11-di-cyclohexylphosphino-12-phenyl-9,10-ethenoanthracene)monophosphines
enhances the performance of this class of ligand in palladium-catalyzed
Suzuki–Miyaura cross-couplings and Buchwald–Hartwig aminations, compared
with their unsubstituted and mono-substituted counterparts. An
alternative complementary synthesis of KITPHOS monophosphines has been
developed and two new members of this family, 2,6-Me2-KITPHOS
[11-dicyclohexylphosphino-12-(2,6-dimethylphenyl)-9,10-ethenoanthracene]
and 2,6-(MeO)2-KITPHOS
[11-dicyclohexylphosphino-12-(2,6-dimethoxyphenyl)-
9,10-ethenoanthracene], have been prepared; palladium complexes of both
are highly efficient catalysts for CC and CN bond formation with a range
of electron-rich and electron-poor aromatic chlorides as well as
heteroaryl chlorides. |
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