29778-30-1Relevant articles and documents
Shuttling Catalyst: Facilitating C?C Bond Formation via Cross-Couplings with a Thermoresponsive Polymeric Ligand
Wang, Erfei,Zhang, Jiawei,Zhong, Zhuoran,Chen, Kaixuan,Chen, Mao
, p. 419 - 423 (2020)
A poly(ethylene glycol) (PEG) linked ortho-MeO-phenyldicyclohexylphosphine (MeO-WePhos) ligand has been synthesized to promote Pd-catalyzed carbon-carbon bond formation by cross-couplings including Sonogashira, Heck, Hiyama and Stille reactions, providing corresponding (hetero)aryl substituted alkynes, alkenes and bi(hetero)aryls in good to excellent isolated yields with low Pd loadings. Facilitated by the lower critical solution temperature behaviour of the polymeric monophosphine ligand, the metal-complex could rapidly shuttle between organic and water phases as regulated by temperature, enabling highly efficient catalyst recycling via a simple phase separation. The chemical structure of ligand was determined by matrix-assisted laser desorption/ionization-time of flight mass spectrometry, nuclear magnetic resonance spectrometry and size-exclusion chromatography measurements. Notably, as demonstrated by the inductively coupled plasma-atomic emission spectrometry measurement, 98% Pd was kept in the water phase after 6 cycles of catalyst recycling experiments. Given the profound impact of transition-metal-catalyzed covalent bond formation and the increasing demand of sustainable chemistry, this work provides an alternative method to conduct cross-couplings with a polymeric shuttling catalyst.
Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions
Dehimat, Zineb Imene,Ya?ar, Sedat,Tebbani, Dahmane,?zdemir, ?smail
, p. 325 - 334 (2017/09/29)
NHC-Pd-PPh3 complexes with the bulky benzyladamantyl substited N-heterocyclic carbene (NHC) were synthesized and characterised by NMR, HRMS and micro analyse. These complexes were proceeded to Sonogashira-Hagihara coupling reaction between aryl
Sonogashira cross-coupling reaction catalysed by mixed NHC-Pd-PPh3 complexes under copper free conditions
Touj, Nedra,Ya?ar, Sedat,?zdemir, Nam?k,Hamdi, Naceur,?zdemir, ?smail
, p. 59 - 71 (2018/02/27)
Mixed NHC–Pd–PPh3 complexes with a methoxyethyl-substituted N-heterocyclic carbene (NHC) were synthesised and characterised by NMR, HRMS, elemental analysis and X-ray crystallography for complex 3b. These complexes were applied to Sonogashira c
