☆ 4.5 Article

[Pd(IPr*R)(acac)Cl]: Efficient bulky Pd-NHC catalyst for Buchwald-Hartwig C-N cross-coupling reaction

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2018)

Journal

JOURNAL OF ORGANOMETALLIC CHEMISTRY

Volume 861, Issue -, Pages 125-130

Publisher

ELSEVIER SCIENCE SA

DOI: 10.1016/j.jorganchem.2018.02.035

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Categories

Chemistry, Inorganic & Nuclear Chemistry, Organic

Funding

Chengdu Xiling Lab Co., Ltd
National Natural Science Foundation of China [21703036]

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Abstract

A series of bulky palladium catalysts based on N-heterocyclic carbene, (Pd(NHC)(acac) Cl: NHC = IPr*me = N, N'-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2 -ylidene, Pd(IPr*me)(acac) Cl; NHC = IPr*ipr = N, N'-bis(2,6-bis(di-4-isopropylphenyl)-4-methylphenyl)-imidazol-2 -ylidene, Pd(IPr*ipr)( acac) Cl; and NHC = IPr*tBu = N, N'-bis(2,6-bis(di-4-(tert-butyl)phenyl)-4-methylphenyl)-imidazol-2-ylidene, Pd(IPr*tBu)(acac) Cl; acac = acetylacetonate), have been designed and synthesized. These three new catalysts showed much better catalytic activity in the Buchwald Hartwig arylamination coupling reaction as compare to the earlier congener (IPr*)Pd(acac) Cl (IPr* = N, N'-bis(2,6-diphenylmethyl)-4-methylphenylimidazol-2-ylidene). The highly active Pd-II precatalyst [Pd(IPr* me)(acac)Cl] has been fully explored by using a wide range of substrates with different electronic and steric demands of coupling partners, for which up to 99% isolated yields were obtained. Remarkably, the moderate isolated yield was obtained for the challenging coupling of the amine bearing very bulky groups. (C) 2018 Published by Elsevier B.V.

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