Copper‐Catalyzed Cross‐Coupling of Boronic Esters with Aryl Iodides and Application to the Carboboration of Alkynes and Allenes

Zhou, Yiqing; You, Wei; Smith, Kevin B.; Brown, M. Kevin

doi:10.1002/anie.201310275

Cited by 243 publications

(80 citation statements)

References 89 publications

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“…Our reaction tolerated a variety of functional groups and proceeded with both electron-rich and electron-poor coupling partners, consistently affording the coupled products in good to excellent yields. Recently, a similar coupling of arylboronate esters with aryl iodides was also reported by Brown et al 31 Consistent with the reactivity trend observed for the coupling of arylsilicon reagents, the reactions of heteroarylboron reagents and heteroaryl iodides proceeded in good to excellent yields by using only 2 mol% copper(I) iodide as catalyst and without requiring the addition of P,N-ligands (Scheme 4). The reaction tolerates functional groups such as CF 3 and ethers on both coupling partners as well as chloride on heteroaryl iodides.…”

Section: Coupling With Organoboron Reagentssupporting

confidence: 69%

Copper-Catalyzed Cross-Couplings of Organometallic Reagents with and without Assistance from PN Ligands

Giri

Thapa

2015

Synlett

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Het)Ar M (Het)Ar X + (Het)Ar (Het)Ar Alkyl/Ar M Ar X + Alkyl/Ar Ar Cu PN-ligand ligand-free M = Si, B, In; X = I, Br NMe 2 R 2 P R = Ph, t-Bu PN Abstract In this article, recent developments of copper-catalyzedcross-couplings are discussed. Critical results that demonstrate the effectiveness of copper catalysts, ligated by P,N-ligands, for cross-coupling reactions are presented to showcase the potential emergence of copper as an alternative to palladium. The observation that the reaction of heteroaryl coupling partners also proceeds under 'ligand-free' conditions holds great promise for developing copper catalysis as a complementary system to palladium catalysis in areas in which palladium either performs unsatisfactorily or requires custom-designed ligands.

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Section: Coupling With Organoboron Reagentssupporting

confidence: 69%

Copper-Catalyzed Cross-Couplings of Organometallic Reagents with and without Assistance from PN Ligands

Giri

Thapa

2015

Synlett

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“…1 H and 13 C NMR spectra and melting point are in agreement with the published data. 12 2 (4 Bromophenyl)naphthalene (4c). Yield 51%, m.p.…”

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confidence: 99%

Synthesis of substituted naphthalenes by GaCl3-mediated cross-dimerization—fragmentation of 2-arylcyclopropane-1,1-dicarboxylates

2014

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“…While carbene ( e. g ., C−M−C) and CO (X−M−CO) ligands still induce the largest shifts toward strong and weak binding, respectively, catalyst with two phosphine ligands (P−M−P) in tandem with a group 11 metal are shifted toward stronger, rather than weaker, binding. This non‐intuitive behavior of phosphine ligands may explain experimental observations of Cu catalyzed Suzuki‐Miyaura C−C cross‐couplings with phosphine ligands . Overall, the clearest route to improving the thermodynamic profiles of group 11 catalysts is including strong σ‐donating ligands that result in stronger binding between the catalyst and the substrate.…”

Section: Resultsmentioning

confidence: 92%

Data Mining the C−C Cross‐Coupling Genome

et al. 2019

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The speed and precision of machine‐learning (ML) techniques in determining quantum chemical properties has resulted in a considerable computational speed up in comparison to traditional quantum chemical methods, and now allows a desired property of thousands of molecules to be assessed virtually instantaneously. The large databases that result from employing ML can, in turn, be mined with the goal of uncovering relationships that may be missed through more commonly used small scale screening procedures. Due to its prominent place in chemistry, catalysis represents a particularly fruitful playground, where drawing connections between the quantum chemical properties of catalysts and their overall catalytic performance may lead to the identification of new, highly functional species. In this spirit, we previously trained ML models to predict the performance of 18000 prospective catalysts for a Suzuki coupling reaction using molecular volcano plots. Here, we apply concepts from big data to probe a type of “C−C cross‐coupling genome” that explores results from many different named cross‐coupling reactions. The use of interactive dimensionality‐reducing data‐clustering maps facilitates the identification of relationships between the thermodynamics of different catalysts and the chemical properties of their constituent metal and ligands. Analyzing large numbers of species in this manner leads to the identification of not only unexpected catalysts that have thermodynamically ideal profiles to catalyze C−C cross‐coupling reactions, but also reveals a wealth of interesting chemical trends regarding the influence played by different metals and ligands, as well as their unique combinations.

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Copper‐Catalyzed Cross‐Coupling of Boronic Esters with Aryl Iodides and Application to the Carboboration of Alkynes and Allenes

Cited by 243 publications

References 89 publications

Copper-Catalyzed Cross-Couplings of Organometallic Reagents with and without Assistance from PN Ligands

Copper-Catalyzed Cross-Couplings of Organometallic Reagents with and without Assistance from PN Ligands

Synthesis of substituted naphthalenes by GaCl3-mediated cross-dimerization—fragmentation of 2-arylcyclopropane-1,1-dicarboxylates

Data Mining the C−C Cross‐Coupling Genome

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