Rhodium-Catalyzed N-Arylation of 2-Pyridones Enabled by 1,6-Acyl Migratory Rearrangement of 2-Oxypyridines.

An efficient rhodium-catalyzed dearomative rearrangement of 2-oxypyridines with quinone diazides has been developed for the direct synthesis of N-arylated pyridones, in which a novel 1,6-O-to-O rather than 1,4-O-to-C acyl rearrangement has been achieved under mild reaction conditions.

[1]  Zhi‐Xiang Yu,et al.  Atroposelective Synthesis of N-Arylindoles via Enantioselective N-H Bond Insertion. , 2022, Organic letters.

[2]  Junheng Liu,et al.  Atroposelective Synthesis of Axially Chiral C2-Arylindoles via Rhodium-Catalyzed Asymmetric C-H Bond Insertion. , 2022, Organic letters.

[3]  Xuesen Fan,et al.  Synthesis of N-Arylindoles from 2-Alkenylanilines and Diazonaphthalen-2(1H)-ones through Simultaneous Indole Construction and Aryl Introduction. , 2022, The Journal of organic chemistry.

[4]  S. You,et al.  SCpRh(III)-Catalyzed Enantioselective Synthesis of Atropisomers by C2-Arylation of Indoles with 1-Diazonaphthoquinones. , 2022, Organic letters.

[5]  Lingheng Kong,et al.  Rhodium-Catalyzed Atroposelective C-H Arylation of (Hetero)Arenes Using Carbene Precursors as Arylating Reagents. , 2022, Organic letters.

[6]  R. Samanta,et al.  Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands. , 2022, Organic letters.

[7]  H. Waldmann,et al.  Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles , 2021, Chemistry.

[8]  Chuan Wang,et al.  Construction of C-C Axial Chirality via Asymmetric Carbene Insertion into Arene C-H Bonds. , 2021, Angewandte Chemie.

[9]  Saikat Roy,et al.  Iridium(III)-Catalyzed Intermolecular Mild N-Arylation of Aliphatic Amides Using Quinoid Carbene: A Migratory Insertion-Based Approach , 2021, ACS Catalysis.

[10]  B. Tan,et al.  Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones , 2021, Science China Chemistry.

[11]  Xinhao Zhang,et al.  Chemo- and Enantioselective Insertion of Furyl Carbene into the N-H Bond of 2-Pyridones. , 2021, Angewandte Chemie.

[12]  Chunnian He,et al.  Highly Atroposelective Rhodium(II)-Catalyzed N–H Bond Insertion: Access to Axially Chiral N-Arylindolocarbazoles , 2021 .

[13]  R. Samanta,et al.  Straightforward Construction and Functionalizations of Nitrogen‐Containing Heterocycles Through Migratory Insertion of Metal‐Carbenes/Nitrenes , 2021, Chemical record.

[14]  S. You,et al.  Oxygen-linked Cyclopentadienyl Rh(III) Complexes-Catalyzed Asymmetric C-H Arylation of Benzo[h]quinolines with 1-Diazonaphthoquinones. , 2021, Angewandte Chemie.

[15]  Y. Shao,et al.  Ruthenium-Catalyzed Chemoselective N-H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides. , 2021, Organic letters.

[16]  Qun Chen,et al.  Dearomative Migratory Rearrangement of 2-Oxypyridines Enabled by α-Imino Rhodium Carbene. , 2020, Organic letters.

[17]  H. Waldmann,et al.  Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex , 2020, Organic letters.

[18]  Y. Lan,et al.  Rh(III)-Catalyzed Asymmetric Access to Spirocycles via C-H Activation and Subsequent Axial-to-Central Chirality Transfer. , 2020, Angewandte Chemie.

[19]  Pirfenidone , 2019, Reactions Weekly.

[20]  Xinhao Zhang,et al.  Access to N-Substituted 2-Pyridones by Catalytic Intermolecular Dearomatization and 1,4-Acyl Transfer. , 2018, Angewandte Chemie.

[21]  N. Cramer,et al.  Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations. , 2018, Angewandte Chemie.

[22]  Julie L. Engers,et al.  Design and Synthesis of N-Aryl Phenoxyethoxy Pyridinones as Highly Selective and CNS Penetrant mGlu3 NAMs. , 2017, ACS medicinal chemistry letters.

[23]  H. Waldmann,et al.  General Enantioselective C-H Activation with Efficiently Tunable Cyclopentadienyl Ligands. , 2017, Angewandte Chemie.

[24]  P. Bharatam,et al.  Copper-Catalyzed N-Arylation of Tautomerizable Heterocycles with Boronic Acids and Its Application to Synthesis of Oxygenated Carbazoles , 2016 .

[25]  T. Hanada,et al.  Discovery of 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel): a novel, noncompetitive α-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist. , 2012, Journal of medicinal chemistry.

[26]  Aaron Petronico,et al.  2-Pyridone and derivatives: gas-phase acidity, proton affinity, tautomer preference, and leaving group ability. , 2012, The Journal of organic chemistry.

[27]  Dean M. Messing,et al.  Discovery of PH-797804, a highly selective and potent inhibitor of p38 MAP kinase. , 2011, Bioorganic & medicinal chemistry letters.

[28]  P. Lam,et al.  Copper-Promoted Carbon-HeteroatomBond Cross-Coupling with Boronic Acids and Derivatives , 2011 .

[29]  H. Mayr,et al.  Ambident reactivities of pyridone anions. , 2010, Journal of the American Chemical Society.

[30]  J. Hartwig.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides. , 2008, Accounts of chemical research.

[31]  S. Buchwald,et al.  Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines. , 2007, Organic letters.

[32]  M. Taillefer,et al.  Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides. , 2004, Chemistry.