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New method for C–H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction

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TLDR
A new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic unbranched and branched aliphatic ethers via activation of C(sp(3))-H.
Abstract
We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic unbranched and branched aliphatic ethers via activation of C(sp3)–H. In the presence of 1 mol% of iron oxide, five and six membered unbranched cyclic ethers such as tetrahydrofuran and tetrahydropyran gave good to excellent yields of cross-coupled products. Whereas, in case of branched ether such as 2-methyltetrahydrofuran, it was observed that the arylation occurred at both the sides and gave moderate yields of a mixture of regioisomers. Among the organometallic species used, alkyl organometallic reagents gave less yields as compared to aryl organometallics.

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Journal ArticleDOI

Iron-Catalyzed C-H Bond Activation.

TL;DR: This review includes reactions that take place via reactive organoiron intermediates, and it covers the reactions of simple substrates and substrates possessing a directing group that anchors the catalyst to the substrate, providing an overview of iron-mediated and iron-catalyzed C-H activation reported in the literature by October 2016.
Journal ArticleDOI

Direct functionalization of tetrahydrofuran and 1,4-dioxane: nickel-catalyzed oxidative C(sp3)-H arylation.

TL;DR: This paper aims to demonstrate the efforts towards in-situ applicability of EMMARM, as to provide real-time information about concrete mechanical properties such as E-modulus and compressive strength.
Journal ArticleDOI

Copper-catalysed oxidative C–H/C–H coupling between olefins and simple ethers

TL;DR: The first copper-catalysed oxidative alkenylation of simple ethers to construct allylic ethers was successfully achieved and it is likely that this reaction is likely to proceed via a radical process.
References
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Journal ArticleDOI

Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

TL;DR: A review of palladium-catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle can be found in this paper.
Journal ArticleDOI

Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation

TL;DR: This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.
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Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

TL;DR: A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
Journal ArticleDOI

Activation of c-h bonds by metal complexes

TL;DR: In this article, it was shown that the same alkylhydridoplatinum(IV) complex is the intermediate in the reaction of ethane with platinum(II) σ-complexes.
Journal ArticleDOI

Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage.

TL;DR: P palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations.
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