Comparison of Arylboron-Based Nucleophiles in Ni-Catalyzed Suzuki–Miyaura Cross-Coupling with Aryl Mesylates and Sulfamates

Zhang, Na; Hoffman, David J.; Gutsche, Nicholas; Gupta, Jayesh; Percéc, Virgil

doi:10.1021/jo300547v

Cited by 78 publications

(54 citation statements)

References 54 publications

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“…A separate study compared the efficiency of cross-coupling of a neopentylboronic ester with that of a pinacol boronic ester in a nickel catalysed SM coupling reaction. 56 It found, in competition experiments, that more of the neopentyl derivative was consumed than the corresponding pinacol ester, thereby implying its greater reactivity. However, both were found to be less efficient than the corresponding trifluoroborate and boronic acid; the latter being the most reactive overall.…”

Section: Properties and Mechanismmentioning

confidence: 99%

Selection of boron reagents for Suzuki–Miyaura coupling

2014

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Suzuki-Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal catalysed carbon-carbon bond forming reaction to date. Its success originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent. A variety of such reagents have been developed for the process, with properties that have been tailored for application under specific SM coupling conditions. This review analyses the seven main classes of boron reagent that have been developed. The general physical and chemical properties of each class of reagent are evaluated with special emphasis on the currently understood mechanisms of transmetalation. The methods to prepare each reagent are outlined, followed by example applications in SM coupling.

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Section: Properties and Mechanismmentioning

confidence: 99%

Selection of boron reagents for Suzuki–Miyaura coupling

2014

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“…In 1997, Indolese reported that Ni(II) complexes can be conveniently reduced to the active Ni(0) species at elevated temperature via the homo-coupling of arylboronic acids under basic conditions. [3,[19][20][21][22][23][24][25] Among these Ni catalysts, Ni(COD) 2 and NiCl 2 (PCy 3 ) 2 are the most popularly used catalysts for Suzuki coupling reactions. [3,[19][20][21][22][23][24][25] Among these Ni catalysts, Ni(COD) 2 and NiCl 2 (PCy 3 ) 2 are the most popularly used catalysts for Suzuki coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Lei

Obregon

Alla

2013

Applied Organom Chemis

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A new nickel(II) s-aryl complex, trans-chloro(9-phenanthrenyl)bis(triphenylphosphine)nickel(II), was used as a precatalyst for the Suzuki-Miyaura coupling reactions of aryl chlorides. The catalytic conditions were optimized by investigating the crosscoupling of p-chloroanisole with phenylboronic acid. The results show that this complex is efficient for both electron-rich and electron-deficient aryl chlorides, though it gives better yields for activated arylboronic acids than deactivated ones. All isolated cross-coupled biaryl products have been characterized by 1 H and 13 C NMR, and their spectral data are consistent with those reported. Side products from the coupling of arylboronic acid with the precatalyst complex have also been isolated and characterized, which is helpful for understanding the coupling mechanism.

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“…The reaction has long been the subject of vast research in transition-metal catalysis. Various transition metal complexes [71,72,73,74,75,76,77,78,79] (e.g., Ni, Au, Co, Cu, etc., as such or combined in pairs as heterobimetallic catalysts), or nonconventional Pd(II)-complexes with intricate organic ligands containing S or Se have been intensively explored [80,81]. Efficient transition metal-free catalysts have also been reported for Suzuki–Miyaura cross-coupling reactions [82].…”

Section: Introductionmentioning

confidence: 99%

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Ding

Yan

et al. 2018

Molecules

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An easy access to a series of previously unreported heterodinuclear Pd-Ln compounds, Pd-bpydc-La, Pd-bpydc-Ce and Pd-bpydc-Nd (bpydc = 2,2′-bipyridine-5,5′-dicarboxylate) has been developed. The Pd-Ln hybrid networks were effectively applied as catalysts in Suzuki–Miyaura C-C cross-coupling reactions of 4-bromoanisole and 4-bromobenzonitrile with phenylboronic acid, under mild conditions. A systematic investigation revealed Pd-bpydc-Nd as the most active catalyst. In all cases, reaction yields varied with the base, catalyst loading and substantially augmented with temperature (from 30 to 60 °C). Substituent effects were operative when changing from 4-bromoanisole to 4-bromobenzonitrile. The key role played by the lanthanides, aromatic substrate and base, in modulating the Pd-catalytic cycle has been highlighted. Importantly, the new catalysts proved to be stable in air and vs. functionalities and are quite efficient in Suzuki–Miyaura carbon-carbon bond formation conducted in protic solvents.

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Comparison of Arylboron-Based Nucleophiles in Ni-Catalyzed Suzuki–Miyaura Cross-Coupling with Aryl Mesylates and Sulfamates

Cited by 78 publications

References 54 publications

Selection of boron reagents for Suzuki–Miyaura coupling

Selection of boron reagents for Suzuki–Miyaura coupling

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

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