Ligand‐Enabled Triple CH Activation Reactions: One‐Pot Synthesis of Diverse 4‐Aryl‐2‐quinolinones from Propionamides

Deng, Youqian; Gong, Wei; He, Jian; Yu, Jin‐Quan

doi:10.1002/ange.201403878

Cited by 35 publications

(10 citation statements)

References 43 publications

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“…224 The monoarylated product of 221 underwent methylene C(sp 3 )–H insertion, followed by β-hydride elimination to generate a cinnamide intermediate. After subsequent Heck coupling with a second aryl iodide, intramolecular C(sp 2 )–H amidation would then provide product 222 .…”

Section: C(sp3)–h Activation Directed By Weakly Coordinating Auxilmentioning

confidence: 99%

Palladium-Catalyzed Transformations of Alkyl C–H Bonds

et al. 2016

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This Review summarizes the advancements in Pd-catalyzed C(sp3)–H activation via various redox manifolds, including Pd(0)/Pd(II), Pd(II)/Pd(IV), and Pd(II)/Pd(0). While few examples have been reported in the activation of alkane C–H bonds, many C(sp3)–H activation/C–C and C–heteroatom bond forming reactions have been developed by the use of directing group strategies to control regioselectivity and build structural patterns for synthetic chemistry. A number of mono- and bidentate ligands have also proven to be effective for accelerating C(sp3)–H activation directed by weakly coordinating auxiliaries, which provides great opportunities to control reactivity and selectivity (including enantioselectivity) in Pd-catalyzed C–H functionalization reactions.

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Section: C(sp3)–h Activation Directed By Weakly Coordinating Auxilmentioning

confidence: 99%

Palladium-Catalyzed Transformations of Alkyl C–H Bonds

et al. 2016

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“…The oxidative addition of C-H bond activated by transition metal has been reported in many recent studies in organometallic chemistry [1][2][3][4]. Benzylic imines (Ph-CH = NR) are the most studied ligands in the cyclometallation of transition metals [5,6].…”

Section: Introductionmentioning

confidence: 99%

Hydridothiazole Rhodium Complexes as a Result of C-H Bond Activation in Iminothiazoles Chelating Ligands

Al-hamidi¹,

Alsaygh²,

Al‐Najjar³

2014

CHEM

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A series of 20 Schiff base ligands derived from 2-aminothiazole and its derivatives and aryl aldehydes with either [RhCl(PPh3)3] or [Rh(µ-Cl)(COD)]2 in the presence of 4 equivalents of PPh3 lead to an Rh(III) cyclometallated complex and the imine ligand (C-H) bond has been added to the metal (C-M-H). The complexes were investigated by using I.R., 1H, 13C and 31P NMR Spectroscopic techniques. The signal of the (C-H) ligand was observed as trans to the nitrogen atom in the complex which is a donor ligand. Graphical Abstract: Total synthesis of hydridothiazole rhodium complexes possessing rhodium hydride signal at δ (-14.60 to-15.04) ppm, trans to N-donor ligand and iminoyl carbon (7C=N) signal in Rh (III) observed at δ (220.1-237.6)ppm, lower field and suggestive of carbine like properties.

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“…[23][24][25][26][27][28][29][30][31] The resultant quinolinone skeleton is prevalent in a large number of bioactive molecules and natural products. [32][33][34] Although various synthetic methods have been developed for their synthesis, [35][36][37][38][39] the present catalytic rearrangement offers a new step-and atom-economical route to access this framework from simple starting materials.…”

Section: Introductionmentioning

confidence: 99%

NHC-Boryl Radical Catalysis for Cycloisomerization With C–C Triple Bond Reorganization

et al. 2019

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Our present study unveils a new and efficient Nheterocyclic carbene (NHC)-boryl radical-catalyzed cycloisomerization of N-(2-ethynylaryl)arylamides. This catalytic process is triggered by the addition of an NHC-boryl radical to the alkynyl moiety, followed by a radical cascade comprising of an intramolecular cyclization, successive 1,5-and 1,2-aryl migrations, and the reorganization of a CC triple bond. Eventually, the catalytic cycle is achieved through a radical β-fragmentation reaction, from which the starting NHC-boryl radical is regenerated, and a structurally important quinolinone framework is assembled. A 13 C-labeling experiment was carried out to verify the CC triple bond reorganization, and the proposed catalytic pathway was supported further by density functional theory calculations. Our identification of NHC-boryl radical as a catalyst, as well as its mode of operation via radical addition/elimination mechanism, would stimulate the advancement of design of radical catalysis and the discovery of novel enantioselective radical-catalyzed processes.

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Ligand‐Enabled Triple CH Activation Reactions: One‐Pot Synthesis of Diverse 4‐Aryl‐2‐quinolinones from Propionamides

Cited by 35 publications

References 43 publications

Palladium-Catalyzed Transformations of Alkyl C–H Bonds

Palladium-Catalyzed Transformations of Alkyl C–H Bonds

Hydridothiazole Rhodium Complexes as a Result of C-H Bond Activation in Iminothiazoles Chelating Ligands

NHC-Boryl Radical Catalysis for Cycloisomerization With C–C Triple Bond Reorganization

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