Cross-Coupling of Remote <i>meta</i>-C–H Bonds Directed by a U-Shaped Template

Wan, Li; Dastbaravardeh, Navid; Li, Gang; Yu, Jin‐Quan

doi:10.1021/ja410760f

Cited by 257 publications

(92 citation statements)

References 44 publications

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“…Fifth, palladium-catalysed oxidative alkenylation provides meta-selective alkenylated products (Fig. 1e) [22][23][24] . Regioselectivity is thus controlled by a well-designed directing group connected to the aromatic ring through a special long linker.…”

mentioning

confidence: 99%

A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate

et al. 2015

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Regioselective C-H bond transformations are potentially the most efficient method for the synthesis of organic molecules. However, the presence of many C-H bonds in organic molecules and the high activation barrier for these reactions make these transformations difficult. Directing groups in the reaction substrate are often used to control regioselectivity, which has been especially successful for the ortho-selective functionalization of aromatic substrates. Here, we describe an iridium-catalysed meta-selective C-H borylation of aromatic compounds using a newly designed catalytic system. The bipyridine-derived ligand that binds iridium contains a pendant urea moiety. A secondary interaction between this urea and a hydrogen-bond acceptor in the substrate places the iridium in close proximity to the meta-C-H bond and thus controls the regioselectivity. (1)H NMR studies and control experiments support the participation of hydrogen bonds in inducing regioselectivity. Reversible direction of the catalyst through hydrogen bonds is a versatile concept for regioselective C-H transformations.

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confidence: 99%

A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate

et al. 2015

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“…[215] Während diese Methode umfassend bei der meta-Arylierung derartiger Substrate zum Einsatz kam, wurde nur eine einzige meta-Methylierung berichtet. Die Durchführbarkeit dieser Vorgehensweise wurde von der Gruppe um Yu demonstriert, die ein abspaltbares,U -fçrmiges Te mplat mit koordinierenden Ni-trilfunktionen entwarf,d as die Aktivierung einer meta-C-H-Bindung in Homobenzylcarboxamiden ermçglichte.…”

Section: Dirigierte Alkylierung Von Homobenzylcarboxamidenunclassified

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

Evano

Theunissen

2019

Angewandte Chemie

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Die Alkylierung von Arenen ist eine der grundlegendsten Transformationen in der chemischen Synthese und führt in vielen wissenschaftlichen Bereichen zu privilegierten Molekülgerüsten. Klassische Methoden für die Einführung von Alkylgruppen in Arene beruhen zumeist auf der Friedel‐Crafts‐Reaktion, Radikaladditionen, Metallierungen oder Präfunktionalisierungen von Arenen; die Anwendungsbreite, Effizienz und Selektivität dieser Methoden sind jedoch begrenzt. Außerdem bauen sie auf der inhärenten Reaktivität des Ausgangsarens auf, die die Alkylierung in einer bestimmten Position bevorzugt und die Einführung von Alkylketten an anderen Stellen wesentlich schwieriger macht. Dieses Problem kann durch die Verwendung einer dirigierenden Gruppe angegangen werden, die in Gegenwart eines Metallkatalysators die regioselektive Alkylierung einer C‐H‐Bindung vereinfacht. Diese dirigierten Alkylierungen von C‐H‐Bindungen in Arenen werden im vorliegenden Aufsatz zusammengefasst.

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“…Using different templates arylation of hydrocinnamic and phenylpropanoic acid derivatives (Scheme 26), and meta C-H olefination of electron rich alcohols and phenols derivatives were carried out (Scheme 27) (66,67). Mechanism for meta C-H activation was proposed based on the KIE study (Scheme 28) and DFT calculations (Fig.…”

Section: Directing Group Assistedmentioning

confidence: 99%

Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

et al. 2015

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Activation/functionalization of inert C-H bond has undergone rapid growth in last decade and provides novel retro-synthetic disconnections for the synthesis of valuable molecules. The selectivity is often achieved by the use of directing group and is mainly limited to the proximal C-H bond. Initially, meta C-H activations were based on electronic or steric control and now it can be achieved by employing nitrile-based end-on-template as the directing group. The compilation of the remote C-H activation strategy will provide the useful linkage to the scientific community. This article is focused on recent progress in remote C-H activation, mechanistic understanding, and its applications in the field of total synthesis of targeted molecules.

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Cross-Coupling of Remote meta-C–H Bonds Directed by a U-Shaped Template

Cited by 257 publications

References 44 publications

A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate

A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

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