Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents

Xu, Guoqiang; Li, Xiaoyan; Sun, Hongjian

doi:10.1016/j.jorganchem.2011.05.017

Cited by 23 publications

(10 citation statements)

References 47 publications

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“…Furthermore, Xu and co‐workers show the possibility to perform Sonogashira couplings with nickel instead of palladium . This process involves the use of Ni II –POCOP pincer complex 88 a as the catalyst for the couplings of alkyl halides with lithium acetylides.…”

Section: Cross‐coupling Reactionsmentioning

confidence: 99%

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

et al. 2018

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Pincer complexes are useful tools for organic synthesis. Their high stability and easy functionalization have allowed the development of novel catalytic systems that have had a tremendous impact in different areas of chemistry. Thus, catalytic reactions are nowadays a fundamental part of several synthetic routes, as they allow “greener” procedures with high atom efficiency. In this context, pincer complexes have contributed to the establishment of novel and efficient catalytic reactions. Thus, herein we summarize the most recent relevant advances involving pincer complexes as catalysts.

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Section: Cross‐coupling Reactionsmentioning

confidence: 99%

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

et al. 2018

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“…Ph P-NiCl was used as a catalyst for the crosscoupling of a series of unactivated alkyl halides with alkynyllithium reagents at room temperature, affording good to excellent yields in most of the cases explored, giving better results as compared to Sonogashira protocols, for instance [103] (Fig. 29).…”

Section: Pocomentioning

confidence: 99%

Recent Advances on the Chemistry of POCOP–Nickel Pincer Compounds

Asay

Morales‐Morales

2015

The Privileged Pincer-Metal Platform: Coordination Chemistry &Amp; Applications

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“…In 2011, an effective C(sp)–C(sp 3 ) bond formation was reported using [NiCl{C 6 H 3 -2,6-(OPPh 2 ) 2 }] as a catalyst (Scheme ). Mori and co-workers subsequently reported the Murahashi reaction to polymerize thiophenes (Scheme ). Following Sun’s Ni-catalyzed C(sp)–C(sp 3 ) Murahashi coupling, Feringa has also reported C(sp 2 )–C(sp 2 ) and C(sp 3 )–C(sp 2 ) bond-forming reaction catalyzed by NiCl 2 (PPh 3 )IPr and NiCl 2 (dppe), respectively .…”

Section: Recent Developmentsmentioning

confidence: 99%

The Resurrection of Murahashi Coupling after Four Decades

et al. 2021

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Since the discovery of the pioneering cross-coupling name reactions in the 1970s, cross-coupling involving organolithium reagents (Murahashi coupling) has been neglected for more than 30 years. It was considered to be a technically nonpractical reaction based on the poor selectivity, because of the high reactivity and low functional group tolerance of the organolithium coupling partner. In this Review, we shall provide a comprehensive update on the renaissance of Murahashi coupling that enabled chemists to overcome many difficulties by using modern catalytic systems, in conjunction with the development of appropriate reaction conditions. As the resurrection of Murahashi coupling has occurred mainly due to Feringa’s work, this transformation may be considered as Murahashi–Feringa coupling.

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Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents

Cited by 23 publications

References 47 publications

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

Recent Advances in Catalysis with Transition‐Metal Pincer Compounds

Recent Advances on the Chemistry of POCOP–Nickel Pincer Compounds

The Resurrection of Murahashi Coupling after Four Decades

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