Abstract:A ruthenium(II)-catalyzed redox-free cycloaddition of N-sulfonyl aromatic aldimines with maleimides providing 1-aminoindanes in good yields is described. Usually, maleimides reacted with substituted aromatics, affording the Michael-type ortho alkylated aromatics or 1,1-type cyclized spirosuccinimides. In the present reaction, maleimides provided 1,2-type cycloaddition products. The proposed mechanism was strongly supported by the DFT calculations and isolation of a ruthenacycle intermediate.
“…In 2018, Jeganmohan reported an efficient synthesis of 1‐aminoindanes through the Ru(II)‐catalyzed cycloaddition of N ‐sulfonyl aromatic aldimines with maleimides (Scheme 38). [41] Dimethyl maleate was also suitable alkylation reagent. In the catalytic reaction, 1,2‐type cycloaddition products were obtained rather than the Michael‐type ortho alkylated aromatics or 1,1‐type cyclized spirosuccinimides.…”
Section: Rutheniummentioning
confidence: 99%
“…In 2018, Jeganmohan reported an efficient synthesis of 1aminoindanes through the Ru(II)-catalyzed cycloaddition of Nsulfonyl aromatic aldimines with maleimides (Scheme 38). [41] Scheme 33. Ru(II)-catalyzed site-selective addition of ortho CÀ H bond of acetophenones or C-2 position of indoles to maleimides.…”
Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, a variety of efficient chelation‐assisted strategies have been employed for the selective addition of C−H bonds to maleimides giving succinimides, which are also highly important building blocks in organic synthesis. This Review provides an overview of research progress relating to maleimides participated transition‐metal‐catalyzed group‐directed C−H alkylation from 2012 to 2021. Significant advances in this field were highlighted, diverse transition metal catalysts, organic substrates contained different directing groups, reaction mechanisms as well as synthetic applications are systematically discussed. In addition, the limitations and intractable issues need to be solved in the future are also pointed out.
“…In 2018, Jeganmohan reported an efficient synthesis of 1‐aminoindanes through the Ru(II)‐catalyzed cycloaddition of N ‐sulfonyl aromatic aldimines with maleimides (Scheme 38). [41] Dimethyl maleate was also suitable alkylation reagent. In the catalytic reaction, 1,2‐type cycloaddition products were obtained rather than the Michael‐type ortho alkylated aromatics or 1,1‐type cyclized spirosuccinimides.…”
Section: Rutheniummentioning
confidence: 99%
“…In 2018, Jeganmohan reported an efficient synthesis of 1aminoindanes through the Ru(II)-catalyzed cycloaddition of Nsulfonyl aromatic aldimines with maleimides (Scheme 38). [41] Scheme 33. Ru(II)-catalyzed site-selective addition of ortho CÀ H bond of acetophenones or C-2 position of indoles to maleimides.…”
Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, a variety of efficient chelation‐assisted strategies have been employed for the selective addition of C−H bonds to maleimides giving succinimides, which are also highly important building blocks in organic synthesis. This Review provides an overview of research progress relating to maleimides participated transition‐metal‐catalyzed group‐directed C−H alkylation from 2012 to 2021. Significant advances in this field were highlighted, diverse transition metal catalysts, organic substrates contained different directing groups, reaction mechanisms as well as synthetic applications are systematically discussed. In addition, the limitations and intractable issues need to be solved in the future are also pointed out.
“…Kim and co‐workers [66] & Jeganmohan [67] and co‐workers employed N ‐sulphonyl aldimines ( 106 ) as substrate with maleimides ( 107 ) as coupling partner to achieve diastereoselective synthesis of ubiquitous scaffold like 1‐aminoindane derivatives ( 108 ) using different reaction conditions as mentioned in Scheme 30. Indanes are biologically significant as having properties like anti‐inflammatory, analgesic, anti‐convulsant etc.…”
Section: The C−c and C−n Bond Formation/annulations Reactionmentioning
Sulphonamides and N‐sulphonyl ketimines/aldimines have turned out to be versatile motifs in the field of synthetic and medicinal chemistry. The field of C−H activation/functionalization flourished remarkably due to their synthetic applicability and directing group plays a remarkable role to achieve regioselectivity in these reactions. The current review summarizes recent tactics by utilizing sulphonamides and N‐sulphonyl ketimines/aldimines as directing groups for C−H activation or functionalization. As a directing group, they also facilitate site selectivity and late‐stage functionalization of drug molecules in order to construct complex scaffolds of therapeutic importance by C−H activation.
“…In addition, the Jeganmohan group showed the Ru-catalyzed cycloaddition of N-sulfonyl aryl aldimines with maleimides (Scheme 88B). 137 The N-sulfonyl directing group and acetate ion sources are crucial for the success of this reaction. This strategy is extended to the construction of succinimide linked oxindoles.…”
Heterocyclic alkenes and their derivatives are an important class of reactive feedstock and valuable synthons. This review highlights the transition-metal-catalyzed coupling of heterocyclic alkenes via a C–H functionalization strategy.
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