Bimetallic catalysis for C–C and C–X coupling reactions

Pye, Dominic R.; Mankad, Neal P.

doi:10.1039/c6sc05556g

Cited by 335 publications

(179 citation statements)

References 109 publications

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“…[7] On the basis of above results and previous reports, [15] a plausible mechanism is illustrated in Scheme 5. Treatment of 3 i with (4-(tert-butyl)phenyl) boronic acid in THF in the presence of PdCl 2 /NiBr 2 (PPh 3 ) 2 and K 3 PO 4 at room temperature successfully afforded the cross-coupling product 6 in 82% yield (Scheme 5).…”

Section: Full Paper Ascwiley-vchdesupporting

confidence: 69%

An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides

Wang

Zhang

et al. 2019

Adv Synth Catal

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Section: Full Paper Ascwiley-vchdesupporting

confidence: 69%

An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides

Wang

Zhang

et al. 2019

Adv Synth Catal

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“…The study of heteropolynuclear complexes with metal-metal interactions between closed-or pseudo-closed-shell metal ions (d 8 ,d 10 ,d 10 s 2 )i safield of great interest. [1] Many of thesei nteractions are dative in nature and are establishedb etween a basic donor metal atom and an acidic acceptorc enter.T he importanceo ft hese dative metallophilic bonds is well recognized, since they are behind many luminescentp roperties.…”

Section: Introductionmentioning

confidence: 99%

“…[10] These polymetallic species can be formed in situ from mononuclear metal complexes,w hich at some point join together to act as the catalyst, or can be added as pre-assembled polymetallicc omplexes. [10] These polymetallic species can be formed in situ from mononuclear metal complexes,w hich at some point join together to act as the catalyst, or can be added as pre-assembled polymetallicc omplexes.…”

Section: Introductionmentioning

confidence: 99%

Pt–M Complexes (M=Ag, Au) as Models for Intermediates in Transmetalation Processes

Baya

Belío

Campillo

et al. 2018

Chemistry A European J

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Heteropolynuclear complexes [(CNC)(PPh )PtM(PPh )]ClO [M=Au (1), Ag (2)] and [{Pt(CNC)(PPh )} M]ClO [M=Ag (3), Au (4); CNC=2,6-diphenylpyridinate] were prepared and studied by X-ray crystallography, spectroscopic techniques, and DFT calculations. The X-ray crystal structures of 1, 3, and 4 confirmed the existence of Pt-M bonds and M⋅⋅⋅C interactions involving one of the phenyl fragments of CNC. Their NMR spectra showed the persistence of the Pt-M interactions in solution and also revealed an intramolecular metronome-like dynamic process consisting of back-and-forth motion of the acidic M fragments along the C-Pt-C axis. DFT calculations on these complexes identified two main orbital interactions between the [PtCNC] and [M] fragments, namely, donation from the former to a vacant orbital of the latter and much weaker backdonation from the acidic M to the Pt fragment. Overall, the strength of the [Pt]⋅⋅⋅M interactions is higher for the gold compounds than for their silver counterparts. The interaction between the acidic center (silver or gold) and the carbon atom of one of the phenylene rings in these heteropolymetallic complexes can be envisaged as the first step in a process of interchange of aryl ligands. However, the ligand exchange cannot progress further due to the polydentate nature of the CNC ligand, and therefore these structures can be considered as frozen snapshots of a transmetalation reaction that has been arrested at different stages of the process.

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“…[1] Tr ansition-metal catalysis enables alkene difunctionalization that proceeds in ah ighly selective and efficient manner. [2] Great advances have been achieved in alkene 1,2-arylborations [3] with an elegant dual metal cooperative catalysis [4] reported by Semba and Nakao and Brown (Figure 1a,l eft). [2] Great advances have been achieved in alkene 1,2-arylborations [3] with an elegant dual metal cooperative catalysis [4] reported by Semba and Nakao and Brown (Figure 1a,l eft).…”

mentioning

confidence: 99%

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

Wang

Ding

et al. 2019

Angewandte Chemie

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An unprecedented arylboration of unactivated terminal alkenes,f eaturing 1,n-regioselectivity,h as been achieved by nickel catalysis.T he nitrogen-based ligand playsa n essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance.Inaddition, the incorporation of ab oron group into the products provides substantial opportunities for further transformations.A lso demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules.Unexpectedly,preliminary mechanistic studies indicate that although the metal migration favors the a-position of boron, selective and decisive bond formation is favored at the benzylic position. Scheme 3. Mechanistic studies. Scheme 4. Proposed mechanism.

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Bimetallic catalysis for C–C and C–X coupling reactions

Abstract: Bimetallic catalysis represents an alternative paradigm for coupling chemistry that complements the more traditional single-site catalysis approach.

Cited by 335 publications

References 109 publications

An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides

An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides

Pt–M Complexes (M=Ag, Au) as Models for Intermediates in Transmetalation Processes

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

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