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Amidation

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Sukbok Chang – One of the best experts on this subject based on the ideXlab platform.

  • direct c h Amidation of benzoic acids to introduce meta and para amino groups by tandem decarboxylation
    Chemistry: A European Journal, 2015
    Co-Authors: Donggun Lee, Sukbok Chang

    Abstract:

    The Ir-catalyzed mild CH Amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional-group compatibility. Subsequent protodecarboxylation of ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)aniline derivatives, the latter being inaccessible by other CH functionalization approaches. The decarboxylation step was compatible with the Amidation conditions, enabling a convenient one-pot, two-step process.

  • iridium catalyzed intermolecular Amidation of sp3 c h bonds late stage functionalization of an unactivated methyl group
    Journal of the American Chemical Society, 2014
    Co-Authors: Taek Kang, Donggun Lee, Zhen Wang, Youngchan Kim, Sukbok Chang

    Abstract:

    Reported herein is the iridium-catalyzed direct Amidation of unactivated sp3 C–H bonds. With sulfonyl and acyl azides as the amino source, the Amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C–H functionalization.

  • iridium catalyzed direct arene c h bond Amidation with sulfonyl and aryl azides
    Journal of Organic Chemistry, 2013
    Co-Authors: Donggun Lee, Youngchan Kim, Sukbok Chang

    Abstract:

    Iridium-catalyzed direct ortho C–H Amidation of arenes has been shown to work well with sulfonyl- and aryl azides as the nitrogen source. The reaction proceeds efficiently with a broad range of substrates bearing conventional directing groups with excellent functional group compatibility under mild conditions. In addition, substrates forming not only 5- but also 6-membered iridacycle intermediates undergo the C–H Amidation with high selectivity.

Akhila K. Sahoo – One of the best experts on this subject based on the ideXlab platform.

  • Sulfoximine Directed Intermolecular o-C–H Amidation of Arenes with Sulfonyl Azides
    Organic Letters, 2013
    Co-Authors: M. Ramu Yadav, Akhila K. Sahoo

    Abstract:

    The Ru(II)-catalyzed intermolecular o-C–H Amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the Amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method is successfully employed for the synthesis of HMR 1766.

  • sulfoximine directed intermolecular o c h Amidation of arenes with sulfonyl azides
    Organic Letters, 2013
    Co-Authors: Ramu M Yadav, Raja K Rit, Akhila K. Sahoo

    Abstract:

    The Ru(II)-catalyzed intermolecular o-C–H Amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the Amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method is successfully employed for the synthesis of HMR 1766.

Chi Ming Che – One of the best experts on this subject based on the ideXlab platform.

  • Reaction mechanism and stereoselectivity of ruthenium-porphyrin-catalyzed intramolecular Amidation of sulfamate ester: A DFT computational study
    Journal of Organic Chemistry, 2008
    Co-Authors: Xufeng Lin, Chi Ming Che, David Lee Phillips

    Abstract:

    The reaction mechanism of the ruthenium–porhyrin complex [Ru(por)(CO)]-catalyzed intramolecular C-H bond Amidation was examined using density functional theory (DFT) calculations. The metal-nitrene reactive intermediate, Ru(por)(CO)-NSO3R1 (R1 = 1-methylclohexl-methyl) was found to be highly favorable to generate in terms of the free energy profile from the reaction of the starting materials. Ru(por)(CO)-NSO3R1 may exist in both singlet and triplet states since they are close in energy. In each state, six C-H bond Amidation reaction pathways were characterized structurally and energetically. The predicted most probable diastereomeric product out of the four possible diasteromeric products examined in the calculations for the Amidation reactions agree well with previously reported experimental results.

  • intermolecular Amidation of unactivated sp2 and sp3 c h bonds via palladium catalyzed cascade c h activation nitrene insertion
    Journal of the American Chemical Society, 2006
    Co-Authors: Hungyat Thu, Chi Ming Che

    Abstract:

    This communication describes the Pd(OAc)2-catalyzed intermolecular Amidation reactions of unactivated sp2 and sp3 C−H bonds using primary amides and potassium persulfate. The substrates containing a pendent oxime or pyridine group were amidated with excellent chemo- and regioselectivities. It is noteworthy that reactive C−X bonds were well-tolerated and a variety of primary amides can be effective nucleophiles for the Pd-catalyzed C−H Amidation reactions. For the reaction of unactivated sp3 C−H bonds, β-Amidation of 1° sp3 C−H bonds versus 2° C−H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C−H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated complex.

  • metalloporphyrin mediated asymmetric nitrogen atom transfer to hydrocarbons aziridination of alkenes and Amidation of saturated c h bonds catalyzed by chiral ruthenium and manganese porphyrins
    Chemistry: A European Journal, 2002
    Co-Authors: Jianglin Liang, Jiesheng Huang, Nianyong Zhu, Chi Ming Che

    Abstract:

    Chiral metalloporphyrins [Mn(Por * )(OH)(MeOH)] (1) and [Ru-(Por * )(CO)(EtOH)] (2) catalyze asymmetric aziridination of aromatic alkenes and asymmetric Amidation of benzylic hydrocarbons to give moderate enantiomeric excesses. The mass balance in these nitrogen-atom-transfer processes has been examined. With PhI=NTs as the nitrogen source, the aziridination of styrenes, trans-stilbene, 2-vinylnaphthalene, indene, and 2,2-dimethylchromene catalyzed by complex 1 or 2 resulted in up to 99 % substrate conversions and up to 94% aziridine selectivities, whereas the Amidation of ethylbenzenes, indan, tetralin, 1-, and 2-ethylnaphthalene catalyzed by complex 2 led to substrate conversions of up to 32% and amide selectivities of up to 91 %. Complex 1 or 2 can also catalyze the asymmetric Amidation of 4-methoxyethylbenzene, tetralin, and 2-ethylnaphthalene with “PhI(OAc) 2 + NH 2 SO 2 Me”, affording the N-substituted methanesulfonamides in up to 56% ee with substrate conversions of up to 34% and amide selectivities of up to 92%. Extension of the “complex 1 + PhI=NTs” or “complex 1 + PhI(OAc) 2 + NH 2 R (R = Ts, Ns)” Amidation protocol to a steroid resulted in diastereoselective Amidation of cholesteryl acetate at the allylic C-H bonds at C-7 with substrate conversions of up to 49% and amide selectivities of up to 90% (α:β ratio: up to 4.2:1). An aziridination- and Amidation-active chiral bis(tosylimido)ruthenium(VI) porphyrin, [Ru(Por * )(NTs) 2 ] (3), and a ruthenium porphyrin aziridine adduct, [Ru(Por * )-(CO)(TsAz)] (4, TsAz = N-tosyl-2-(4-chlorophenyl)aziridine), have been isolated from the reaction of 2 with PhI=NTs and N-tosyl-2-(4-chlorophenyl)aziridine, respectively. The imidoruthenium porphyrin 3 could be an active species in the aziridination or Amidation catalyzed by complex 2 described above. The second-order rate constants for the reactions of 3 with styrenes, 2-vinylnaphthalene, indene, ethylbenzenes, and 2-ethylnaphthalene range from 3.7-42.5 × 10 – 3 dm 3 mol – 1 s – 1 . An X-ray structure determination of complex 4 reveals an O- rather than N-coordination of the aziridine axial ligand. The fact that the N-tosylaziridine in 4 does not adopt an N-coordination mode disfavors a concerted pathway in the aziridination by a tosylimido ruthenium porphyrin active species.