Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation

Dennis, Joseph M.; Compagner, Chad; Dorn, Stanna K.; Johnson, J. J.

doi:10.1021/acs.orglett.6b01434

Cited by 39 publications

(16 citation statements)

References 41 publications

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“…In addition, use of aryl amides, ammonium salts and nitro compounds has also been demonstrated via a metal-mediated C–N bond activation . Apart from cleaving the more polarized C–X (X = halogen), C–O and C–N bonds, SMC reactions via activation of less polar, unstrained C–C bonds in common feedstock would be highly valuable, which, however, remain a challenge to date. , …”

mentioning

confidence: 99%

Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds

2018

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Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.

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confidence: 99%

Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds

2018

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“…Quinolinyl ketones are regarded as a versatile directing group by the cooperation of transition metal catalysts for activating the organic transformation [77][78][79][80][81][82]. A variety of 2-aminobenzophenone 4 were subjected to react with propionaldehyde 2a in the optimized reaction condition.…”

Section: Resultsmentioning

confidence: 99%

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

2021

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Herein, we report a facile synthetic methodology for the preparation of 2,3-dialkylquinolines from anilines and propionaldehydes. This cyclization involved environmentally friendly Nafion® NR50 as an acidic catalyst with microwave irradiation as the heating source. A series of substituted 2-ethyl-3-methylquinolines were prepared from various anilines and propionaldehyde derivatives through this protocol with good to excellent yields. Some new chemical structures were confirmed by X-ray single-crystal diffraction analysis and the related data were provided. The plausible reaction mechanism studies are also discussed.

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“…42 Through developing new C-C activation methods, the scope of electrophiles that can undergo cross couplings has been extended to less polar compounds. Previously, ketones with high ring strain 43 or a permanent DG 44,45 were used as electrophiles in Suzuki-Miyaura coupling (SMC) reactions. By employing the temporary DG strategy, Dong and coworkers developed the SMC reactions of simple unstrained ketones with arylboronates via cleavage of the α C−C bonds of ketones (FIG 4A).…”

Section: Intermolecular Cross-couplingsmentioning

confidence: 99%

“…The reaction mechanism has been explored via both experimental and computational studies. It was proposed that the rhodium-bisphosphinite complex 62 first reacts with hydrogen to form a rhodium On the other hand, heterocycles such as pyridine [70][71][72][73][74] and quinoline 44,45,51,52 derivatives have been frequently used as DGs in the activation of unstrained C−C bonds. Compared to imine or phosphinite-type DGs that are easily removable by hydrolysis, heterocycle-based DGs were generally considered to be stable and only a few of them can be removed via simple post-chemical transformations.…”

Section: Dgs Removed Via Post-chemical Transformationsmentioning

confidence: 99%

Temporary or removable directing groups enable activation of unstrained C–C bonds

2020

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Carbon−carbon (C-C) bonds constitute basic skeletons in most organic molecules. One can imagine that selective manipulation of C-C bonds would provide a direct approach to edit or alter molecular scaffolds but has been an ongoing challenge. Due to the kinetic inertness of C-C bonds, the common strategies of activating these bonds by transition metals rely on either the use of highly strained substrates or the assistance of a permanent directing group (DG), in which strain relief or formation of stable metallocycles becomes the driving force. To allow more common and less strained compounds utilized as substrates for C-C activation, the use of temporary and removable DGs has emerged as an attractive strategy in the past two decades. A variety of C−C bonds in unstrained or less strained organic molecules now can be converted to more reactive metal-carbon bonds, and further downstream transformations have led to diverse synthetic methods. This review highlights the development of catalytic approaches that can activate unstrained C-C bonds enabled by temporary or removable DGs. The content is mainly divided based on the nature of the DGs: temporary and removable. Applications of these methods in syntheses of natural products or bioactive molecules are also discussed.

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Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation

Cited by 39 publications

References 41 publications

Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds

Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

Temporary or removable directing groups enable activation of unstrained C–C bonds

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