Ruthenium-Catalyzed Intramolecular Hydroarylation of Arenes and Mechanistic Study: Synthesis of Dihydrobenzofurans, Indolines, and Chromans

Rit, Raja K.; Ghosh, Koushik; Mandal, Rajib; Sahoo, Akhila K.

doi:10.1021/acs.joc.6b01734

Cited by 33 publications

(8 citation statements)

References 55 publications

(21 reference statements)

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“…While enantioselective hydroarylation has been successfully developed for the syntheses of other related cyclic skeletons, the enantioselective synthesis of indolines has been underdeveloped. ,,,, Of particular relevance, Bergman and Ellman demonstrated a synthesis of a functionalized dihydrofuran in 45% ee using 30 mol % of a chiral amine cocatalyst in a Rh(I)-catalyzed intramolecular hydroarylation . Recent disclosure of Ru(II) as an effective catalyst for intramolecular hydroarylation encourages the development of the potential enantioselective processes . Considering the cost-effectiveness and the availability of the simple Ru(II) arene complexes, identifying a suitable imine-based CTDG strategy seems practical.…”

mentioning

confidence: 99%

Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives

Lakmal

Qian

et al. 2019

J. Am. Chem. Soc.

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Ru(II)-catalyzed enantioselective C−H activation/hydroarylation has been developed for the first time, allowing for highly enantioselective synthesis of indoline derivatives via catalytic C−H activation. Commercially available Ru(II) arene complexes and chiral α-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multisubstituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enables access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.

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mentioning

confidence: 99%

Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives

Lakmal

Qian

et al. 2019

J. Am. Chem. Soc.

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“…Both hydroarylation and amino carbonylation–cyclization sequences are redox neutral process. Cu(OAc) 2 serves as the base for the hydroarylation reaction and is regenerated during the protodemetalation; thus, the catalytic amount of copper salt is sufficient . Upon further screenings of the reaction parameter, 20 mol % Cu(OAc) 2 was found sufficient.…”

Section: Resultsmentioning

confidence: 99%

Sulfoximine-Assisted Unsymmetrical Twofold C–H Functionalization of Arenes

Ghosh

Mukherjee

et al. 2020

J. Org. Chem.

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An unprecedented ruthenium (Ru)-catalyzed twofold unsymmetrical annulation of 3-O/N-allyl benzoic acid derivatives with isocyanates for the construction of dihydro-furan/indole-fused phthalimide scaffolds is discussed. This double-unsymmetrical functionalization of both o,o'-C−H bonds of arene moiety is explicitly viable under the influence of methylphenyl sulfoximine directing group constructing three different [C−C/C−C(O)/N−C(O)] bonds under a single catalytic system. A broad scope with all six-carbon-substituted arene motifs, control experiments, and gram-scale synthesis make the synthetic model viable and significant.

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“…Later, Sahoo's group explored the synthetic potential and the utility of the Ru‐catalyzed intramolecular hydroarylation of arenes and reported the amide‐directed intramolecular hydroarylation of O‐/N‐tethered olefin bearing benzamide derivatives (Scheme 12). [25] The catalytic reaction works well in presence of 3 mol% [RuCl 2 ( p ‐cymene)] 2 complex, AgSbF 6 (12‐20 mol%) and Mn(OAc) 2 (25–50 mol%) at 70–110 °C in DCE. This method has proved to be very proficient in the synthesis of dihydrobenzofuran, indoline, and chroman skeletons in good to excellent yield (up to 98%).…”

Section: Intramolecular C−c Bond Formationmentioning

confidence: 94%

Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

Singh

Chouhan

Mukherjee

2021

Chemistry An Asian Journal

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Ruthenium catalyzed C−H activation is well known for its high tolerance towards the functional group and broad applicability in organic synthesis and molecular sciences, with significant applications in pharmaceutical industries, material sciences, and polymer industry. In the last few decades, enormous progress has been observed with ruthenium‐catalyzed C−H activation chemistry. Notably, the vast majority of the C−H functionalization known in the literature are intermolecular, although the intramolecular variant provides fascinating new structural facet starting from the simple molecular scaffolds. Intramolecular C−H functionalization is atom economical and step efficient, results in less formation of undesired products which is easy to purify. This has created a lot of interest in organic chemistry in developing new synthetic strategies for such functionalization. The focus of this review is to present the relatively unexplored intramolecular functionalization of C−H bonds into C−X (X=C, N, O, S) bonds utilizing versatile ruthenium catalysts, their scope, and brief mechanistic discussion.

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Ruthenium-Catalyzed Intramolecular Hydroarylation of Arenes and Mechanistic Study: Synthesis of Dihydrobenzofurans, Indolines, and Chromans

Cited by 33 publications

References 55 publications

Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives

Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives

Sulfoximine-Assisted Unsymmetrical Twofold C–H Functionalization of Arenes

Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

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