Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 1, Pages 201-211Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900577
Keywords
aryl chlorides; Buchwald-Hartwig aminations; electron-rich species; KITPHOS biaryl-like monophosphines; Suzuki-Miyaura coupling
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Funding
- EPSRC
- Engineering and Physical Sciences Research Council [EP/F03637X/1] Funding Source: researchfish
- EPSRC [EP/F03637X/1] Funding Source: UKRI
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ortho,ortho'-Substitution of the phosphinoalkyne-derived aryl ring in KITPHOS (11-dicyclohexylphosphino-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-Me-2-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 C-C and C-N bond formation with a range of electron-rich and electron-poor aromatic chlorides as well as heteroaryl chlorides.
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