2011
DOI: 10.1039/c1cs15013h
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Recent developments in natural product synthesis using metal-catalysed C–H bond functionalisation

Abstract: Metal-catalysed C-H bond functionalisation has had a significant impact on how chemists make molecules. Translating the methodological developments to their use in the assembly of complex natural products is an important challenge for the continued advancement of chemical synthesis. In this tutorial review, we describe selected recent examples of how the metal-catalysed C-H bond functionalisation has been able to positively affect the synthesis of natural products.

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Cited by 1,539 publications
(237 citation statements)
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“…7,8,174180 Furthermore, aliphatic C–H bonds are one of the least reactive functional groups in organic chemistry, as their stability to most reaction conditions has informed the strategies of chemical synthesis, in targeting more traditionally reactive chemical handles, for centuries. 177 Hence, it is a substantial challenge to override a reagent’s or catalyst’s propensity to react with customarily more activated functional groups, such as alkenes, alcohols, or carbonyls, in order to achieve C–H bond functionalizations. Moreover, owing to their low polarity, most C–H bonds are chemically similar, which requires catalysts to differentiate between extremely subtle electronic and steric variations among a myriad of comparable bonds.…”
Section: C–h Oxidationmentioning
confidence: 99%
“…7,8,174180 Furthermore, aliphatic C–H bonds are one of the least reactive functional groups in organic chemistry, as their stability to most reaction conditions has informed the strategies of chemical synthesis, in targeting more traditionally reactive chemical handles, for centuries. 177 Hence, it is a substantial challenge to override a reagent’s or catalyst’s propensity to react with customarily more activated functional groups, such as alkenes, alcohols, or carbonyls, in order to achieve C–H bond functionalizations. Moreover, owing to their low polarity, most C–H bonds are chemically similar, which requires catalysts to differentiate between extremely subtle electronic and steric variations among a myriad of comparable bonds.…”
Section: C–h Oxidationmentioning
confidence: 99%
“…[1][2][3][4][5][6][7] A relatively inert C-H bond is activated, and the hydrogen atom acts essentially as a leaving group. This technology allows one to bypass the installation and subsequent removal of classical leaving groups and to reduce wastes as well as some precautions (such as protecting group manipulations) typical in the handling of promiscuous amine reagents.…”
Section: Introductionmentioning
confidence: 99%
“…In the last years, selective catalytic oxidations of unactivated C-H bonds have attracted great attention: this approach, if implemented on preparative scale, could provide easy and efficient methodologies for the directed introduction of oxygen atom into complex organic molecules at late stages of multistep syntheses, on the basis of novel synthetic strategies [1][2][3][4][5][6][7][8][9][10][11]. Selective C-H oxidation reactions may lead to formation of new C-C and C-X (e.g., C-O, C-N, C-S, C-halogen, etc.…”
Section: Introductionmentioning
confidence: 99%