Solvent-free and room temperature microwave-assisted direct C7 allylation of indolines <i>via</i> sequential C–H and C–C activation

Wang, Qiuling; Shi, Linlin; Liu, Shuang; Zhi, Changlei; Fu, Lian-Rong; Zhu, Xinju; Hao, Xin‐Qi; Song, Mao‐Ping

doi:10.1039/d0ra02016h

Cited by 16 publications

(10 citation statements)

References 66 publications

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“…Our group has been interested in functionalization of biologically important heterocyclic frameworks. We have developed C7-functionalized indolines via chelation-assisted strategy . Meanwhile, Cu-mediated direct C–H sulfonylation of benzoic acids with TosMIC has also been reported using a PyO-directing group .…”

Section: Introductionmentioning

confidence: 99%

Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)

Wang

Ren

et al. 2021

J. Org. Chem.

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An iron-mediated highly selective C–H sulfonylmethylation of aniline derivatives with p-toluenesulfonylmethyl isocyanide in a mixture solvent of H2O and PEG400 under an Ar atmosphere has been realized. This transformation proceeds with operational convenience, use of earth-abundant metal catalyst and nontoxic media, broad substrate scope, and good functional group tolerance. The current methodology could be applied to the regioselective C–H sulfonylmethylation of indolines, tetrahydroquinolines, and tertiary anilines.

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Section: Introductionmentioning

confidence: 99%

Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)

Wang

Ren

et al. 2021

J. Org. Chem.

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“…The optimal reaction conditions included 20 mol% of AgSbF 6 in order to form cationic Rh(III) species in situ and 30 mol% of 1-adamantane carboxylic acid as an additive to promote the metalation step. Further work on this reaction pointed to the possibility to carry out this transformation at room temperature in solvent-free and microwave-assisted conditions through Ru-catalysis [ 45 ].…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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“…68 Very recently, the group of Song established a pathway for a neat C(7)-allylation of indolines under microwave energy (Scheme 23). 69 They initiated the investigation by choosing indolines and VCP (vinyl cyclopropane) as model substrates using microwave irradiation. The functionalized product was isolated in 40% yield in the presence of [Ru( p-cymene)Cl 2 ] 2 (5 mol%), AgSbF 6 (25 mol%), and AdCOOH (30 mol%) at 25 °C for about an hour.…”

Section: Mw-assisted C-h Activation In Solvent-free Conditionsmentioning

confidence: 99%

Sustainable C–H functionalization under ball-milling, microwave-irradiation and aqueous media

et al. 2022

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Solvent-free and room temperature microwave-assisted direct C7 allylation of indolines via sequential C–H and C–C activation

Abstract: A Ru or Rh-catalyzed direct C7 allylation of indolines with vinylcyclopropanes via sequential C–H/C–C activation under microwave irradiation has been disclosed.

Cited by 16 publications

References 66 publications

Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)

Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Sustainable C–H functionalization under ball-milling, microwave-irradiation and aqueous media

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