Biaryl Construction Based on Nickel-Catalyzed C–O Bond Activation

Diao, Haiyan; Shi, Zhang‐Jie; Liu, Feng

doi:10.1055/a-1349-3543

Cited by 3 publications

(2 citation statements)

References 57 publications

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“…10b Although palladium has demonstrated success in catalyzing cross-couplings of aryl tosylates, 12,32 nickel has developed a reputation for reacting more easily with strong C-O bonds due to its smaller size and greater nucleophilicity. 33 Despite a flurry of reports on Ni-catalyzed cross-couplings of phenol derivatives in the last 20 or so years, few of these methods permit selective cleavage of a C-O bond in the presence of aryl-halogen bonds. [33][34][35] Consequently, we have been interested in systematically exploring the influence of ligands on the chemoselectivity of nickel, with a particular interest in achieving C-O-selective Suzuki coupling of chlorinated phenol derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…33 Despite a flurry of reports on Ni-catalyzed cross-couplings of phenol derivatives in the last 20 or so years, few of these methods permit selective cleavage of a C-O bond in the presence of aryl-halogen bonds. [33][34][35] Consequently, we have been interested in systematically exploring the influence of ligands on the chemoselectivity of nickel, with a particular interest in achieving C-O-selective Suzuki coupling of chlorinated phenol derivatives. This selectivity had not been previously achieved for Suzuki couplings of nontriflate phenol derivatives using nickel catalysts.…”

Section: Introductionmentioning

confidence: 99%

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C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives

Russell¹,

Neufeldt²

2021

Synlett

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Chemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C—O-selective Ni-catalyzed Suzuki-Miyaura coupling of chloroaryl tosylates is discussed in detail. 1. Introduction 2. DFT Studies on Oxidative Addition at Ni(0) 3. Stoichiometric Oxidative Addition Studies 4. Development of a Tosylate-Selective Suzuki Coupling 5. Conclusion and Outlook

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives

Russell¹,

Neufeldt²

2021

Synlett

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Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C–O Bond

et al. 2021

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The pioneering nickel-catalyzed cross-coupling of C–O electrophiles was unlocked by Wenkert in the 1970s; however, the transition-metal-catalyzed asymmetric activation of aromatic C–O bonds has never been reported. Herein the first enantioselective activation of an aromatic C–O bond is demonstrated via the catalytic arylative ring-opening cross-coupling of diarylfurans. This transformation is facilitated via nickel catalysis in the presence of chiral N-heterocyclic carbene ligands, and chiral 2-aryl-2′-hydroxy-1,1′-binaphthyl (ArOBIN) skeletons are delivered axially in high yields with high ee. Moreover, this versatile skeleton can be transformed into various synthetic useful intermediates, chiral catalysts, and ligands by using the CH- and OH-based modifiable sites. This chemistry features mild conditions and good atom economy.

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Machine Learning Yield Prediction from NiCOlit, a Small-Size Literature Data Set of Nickel Catalyzed C–O Couplings

et al. 2022

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Synthetic yield prediction using machine learning is intensively studied. Previous work focused on two categories of datasets: High-Throughput Experimentation data, as an ideal case study and datasets extracted from proprietary databases, which are known to have a strong reporting bias towards high yields. However, predicting yields using published reaction data remains elusive. To fill the gap, we built a dataset on 1 nickel-catalyzed cross-couplings extracted from organic reaction publications, including scope and optimization information. We demonstrate the importance of including optimization data as a source of failed experiments and emphasize how publication constraints shape the exploration of the chemical space by the synthetic community.While machine learning models still fail to perform out-of-sample predictions, this work shows that adding chemical knowledge enables fair predictions in a low-data regime.Eventually, we hope that this unique public database will foster further improvements of machine learning methods for reaction yield prediction in a more realistic context.

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Biaryl Construction Based on Nickel-Catalyzed C–O Bond Activation

Cited by 3 publications

References 57 publications

C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives

C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives

Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C–O Bond

Machine Learning Yield Prediction from NiCOlit, a Small-Size Literature Data Set of Nickel Catalyzed C–O Couplings

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