2021
DOI: 10.1002/ajoc.202000584
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Transition‐Metal‐Free C−H Silylation: An Emerging Strategy

Abstract: Silicon‐containing molecules are of great interest with widespread applications in several research areas such as polymer chemistry, materials science, medicinal chemistry, and complex molecule synthesis. Transition‐metal‐free C−H silylation is an essential process because this process is useful in fabricating carbon‐silicon bonds which can be further transformed into a number of other compounds. Since transition‐metal‐catalyzed C−H bond silylation is a developed field, therefore this context only contains tra… Show more

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Cited by 26 publications
(8 citation statements)
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“…Hydroxylated N -heteroarenes and phenols with electron-withdrawing functional groups are valuable synthetic intermediates and are prevalent in bioactive and other functional compounds (Figure ). The most practiced routes to install hydroxyl groups on such arenes require prefunctionalized starting materials, most commonly through S N Ar or metal-catalyzed hydroxylation of (hetero)­aryl halides or oxidation of (hetero)­aryl boronates and silanes. Significant advances in C–H borylation and silylation thus provide a multistep means of net C–H hydroxylation for a broad range of (hetero)­arenes, with reviews on the selectivity and scope available. , Methods for installing alternative functional handles, such as halogen or phosphonium groups, as well as Ritter’s C–H oxymesylation protocol, can also be leveraged to access to these classes of hydroxy­(hetero)­arenes . As a more streamlined route, direct C–H hydroxylation of electron-deficient aromatic compounds represents an attractive yet underdeveloped reaction.…”
Section: Introductionmentioning
confidence: 99%
“…Hydroxylated N -heteroarenes and phenols with electron-withdrawing functional groups are valuable synthetic intermediates and are prevalent in bioactive and other functional compounds (Figure ). The most practiced routes to install hydroxyl groups on such arenes require prefunctionalized starting materials, most commonly through S N Ar or metal-catalyzed hydroxylation of (hetero)­aryl halides or oxidation of (hetero)­aryl boronates and silanes. Significant advances in C–H borylation and silylation thus provide a multistep means of net C–H hydroxylation for a broad range of (hetero)­arenes, with reviews on the selectivity and scope available. , Methods for installing alternative functional handles, such as halogen or phosphonium groups, as well as Ritter’s C–H oxymesylation protocol, can also be leveraged to access to these classes of hydroxy­(hetero)­arenes . As a more streamlined route, direct C–H hydroxylation of electron-deficient aromatic compounds represents an attractive yet underdeveloped reaction.…”
Section: Introductionmentioning
confidence: 99%
“…Silylacetylenes (alkynylsilanes) have found broad use in synthesis and thus are of great interest to the scientific community. [1][2][3] Indeed, these compounds wherein the silyl moiety is directly bonded to the sp-carbon bond can be readily converted into other functionalities via several pathways, including cross-coupling reactions, Diels-Alder cyclization, cycloadditions, and others (Figure 1, a). [1,4] Moreover, typically, a direct sp CÀ H silylation (mainly trimethylsilylation) arguably represents an important strategy for the protection of the reactive terminal C�CÀ H bonds.…”
Section: Introductionmentioning
confidence: 99%
“…As an alternative approach, transition-metal-free systems have also been scrutinized (Scheme A). , For instance, Grubbs and Stoltz reported a C2-selective silylation of heteroaromatics by using a KO t Bu catalyst. , While this reaction was proposed to proceed via an electrophilic aromatic substitution (S E Ar), the scope was limited mainly to electron-rich N-heteroarenes such as indoles. Simchen et al showcased the use of a Me 3 SiOTf silylating reagent in combination with excessive bases for the selective C3-silyation of indoles and pyrroles .…”
mentioning
confidence: 99%