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ortho,ortho'-Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium-Catalyzed C‒C and C‒N Bond Formation

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

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.


Publication metadata

Author(s): Doherty S, Knight JG, McGrady JP, Ferguson AM, Ward NAB, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Advanced Synthesis & Catalysis

Year: 2010

Volume: 352

Issue: 1

Pages: 201-211

Date deposited: 07/06/2010

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - V C H Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/adsc.200900577

DOI: 10.1002/adsc.200900577


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