Nickel‐Catalyzed C−H Heteroarylation of Chiral Oxazolines

Lu, Peng; Ji, Chong‐Lei; Lu, Zhan

doi:10.1002/ajoc.201700446

Cited by 8 publications

(10 citation statements)

References 84 publications

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“…The bidentate phosphine 1,1′-bis(diphenylphosphino)methane (DPPM) leads to a moderately low yield of 36%, and PPh 3 is even lower at 8%. Other MBr 2 compounds, such as FeBr 2 , CoBr 2 , and CuBr 2 , give no yield …”

Section: Cross-couplingmentioning

confidence: 99%

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Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

et al. 2020

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A critically important process in catalysis is the formation of an active catalyst from the combination of a metal precursor and a ligand, as the efficacy of this reaction governs the amount of active catalyst. This Review is a comprehensive overview of reactions catalyzed by nickel and an added bidentate phosphine, focusing on the steps transforming the combination of precatalyst and ligand into an active catalyst and the potential effects of this transformation on nickel catalysis. Reactions covered include common cross-coupling reactions, such as Suzuki, Heck, Kumada, and Negishi couplings, addition reactions, cycloadditions, C−H functionalizations, polymerizations, hydrogenations, and reductive couplings, among others. Overall, the most widely used nickel precatalyst with free bidentate phosphines is Ni(cod) 2 , which accounts for ∼50% of the reports surveyed, distantly followed by Ni(acac) 2 and Ni(OAc) 2 , which account for ∼10% each. By compiling the reports of these reactions, we have calculated statistics of the usage and efficacy of each ligand with Ni(cod) 2 and other nickel sources. The most common bidentate phosphines are simple, relatively inexpensive ligands, such as DPPE, DCPE, DPPP, and DPPB, along with others with more complex backbones, such as DPPF and Xantphos. The use of expensive chiral phosphines is more scattered, but the most common ligands include BINAP, Me-Duphos, Josiphos, and related analogs.

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Section: Cross-couplingmentioning

confidence: 99%

“…Other MBr 2 compounds, such as FeBr 2 , CoBr 2 , and CuBr 2 , give no yield. 192 2.3.6. Phenyl Anion.…”

Section: Carbonmentioning

confidence: 99%

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

et al. 2020

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“…Inspired by earlier contributions by Itami and Miura on nickel-catalyzed C–H functionalizations of oxazolinones, , Lu reported on a nickel-catalyzed C–H heteroarylation of chiral oxazolines 977 with heteroaryl halides 135 (Scheme ). In addition to a series of thiophenes, quinolines, and bipyridines, 2-bromo-6-iminopyridines could be also functionalized in high yields, enabling a straightforward synthesis of multidentate , chiral ligands …”

Section: Nickelmentioning

confidence: 99%

“…Inspired by earlier contributions by Itami and Miura on nickel-catalyzed C−H functionalizations of oxazolinones, 1265,1266 Lu reported on a nickel-catalyzed C−H heteroarylation of chiral oxazolines 977 with heteroaryl halides 135 (Scheme 540). 1290 In addition to a series of thiophenes, quinolines, and bipyridines, 2-bromo-6-iminopyridines could be also functionalized in high yields, enabling a straightforward synthesis of multidentate 1291,1292 chiral ligands. 1290 The Chatani group developed an approach for the nickel(II)-catalyzed direct arylation of aromatic amides 278 with aryl iodides 693 exploiting a N,N-bidentate chelation assistance (Scheme 541).…”

Section: Scheme 505 Pincer Nickel(ii)-catalyzed C−h Bond Alkylation O...mentioning

confidence: 99%

“…1290 In addition to a series of thiophenes, quinolines, and bipyridines, 2-bromo-6-iminopyridines could be also functionalized in high yields, enabling a straightforward synthesis of multidentate 1291,1292 chiral ligands. 1290 The Chatani group developed an approach for the nickel(II)-catalyzed direct arylation of aromatic amides 278 with aryl iodides 693 exploiting a N,N-bidentate chelation assistance (Scheme 541). 1293 Notably, among various directing groups only the 8-aminoquinoline auxiliary gave the desired products 332.…”

Section: Scheme 505 Pincer Nickel(ii)-catalyzed C−h Bond Alkylation O...mentioning

confidence: 99%

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3d Transition Metals for C–H Activation

et al. 2018

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C−H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material sciences, crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these C−H functionalizations required precious 4d or 5d transition metal catalysts. Given the cost-effective and sustainable nature of earth-abundant first row transition metals, the development of less toxic, inexpensive 3d metal catalysts for C−H activation has gained considerable recent momentum as a significantly more environmentally-benign and economically-attractive alternative. Herein, we provide a comprehensive overview on first row transition metal catalysts for C−H activation until summer 2018.

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Single‐Electron‐Transfer‐Initiated Sequential Direct Arylation Reaction of Pyrrole with Aryl Diazonium Salts

2019

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Direct and sequential arylations of pyrrole with a diazonium salt were initiated by single electron transfer from cobaltocene. The direct arylation reaction of pyrrole was completed within 30 min even at room temperature and the corresponding arylated product was obtained in good yield. The second arylation reaction of monoarylated heteroarenes also proceeded successfully and moderate to good yields of diarylated pyrroles were obtained. A gramscale reaction also proceeded without decreasing the yield of the product.[a] Dr.

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Nickel‐Catalyzed C−H Heteroarylation of Chiral Oxazolines

Abstract: A nickel‐catalyzed C−H heteroarylation at the 2 position of oxazolines with heteroaryl halides was developed. Various oxazoline‐containing multidentate chiral ligands have been efficiently synthesized.

Cited by 8 publications

References 84 publications

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

3d Transition Metals for C–H Activation

Single‐Electron‐Transfer‐Initiated Sequential Direct Arylation Reaction of Pyrrole with Aryl Diazonium Salts

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