Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids

Zhao, Sheng; Chen, Fa‐Jie; Liu, Bin; Shi, Bing‐Feng

doi:10.1007/s11426-015-5376-z

Cited by 22 publications

(3 citation statements)

References 27 publications

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“…In subsequent studies, Shi and Chen introduced the 2-pyridylethylamine (PE) or 2-pyridylisopropylamine (PIP) derived N , N -bidnetate directing group. A variety of functionalization reactions including C–C ,− or C–heteroatom bond − formation reactions have been subsequently reported to date using various metal catalysts, including Pd, Co, Cu, and Ru. In this section, we summarized the available literature reports dealing with C–C bond formation reactions that involve these PM, PE, and PIP directing groups.…”

Section: Nn-bidentate Directing Groupsmentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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During the past decades, synthetic organic chemistry discovered that directing group assisted C−H activation is a key tool for the expedient and siteselective construction of C−C bonds. Among the various directing group strategies, bidentate directing groups are now recognized as one of the most efficient devices for the selective functionalization of certain positions due to fact that its metal center permits fine, tunable, and reversible coordination. The family of bidentate directing groups permit various types of assistance to be achieved, such as N,N-dentate, N,O-dentate, and N,S-dentate auxiliaries, which are categorized based on the coordination site. In this review, we broadly discuss various C− H bond functionalization reactions for the formation of C−C bonds with the aid of bidentate directing groups.

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Section: Nn-bidentate Directing Groupsmentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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“…Further developments in this process set the stage for the copper-catalyzed C−H benzoxylation of 2arylpyridines 24 to convert different arylcarboxy surrogates, such as sodium carboxylates, 1814 aldehydes, 1815 methyl arenes, 1815 benzyl alcohols/benzyl amines, 1816,1817 and terminal aryl alkenes and alkynes 1818 (Table 4). In addition to pyridine-directed arene C−H functionalizations, coppercatalyzed acyloxylation has been demonstrated for amides 1819,1820 and heterocycle N-oxides 1821 as well.…”

Section: Scheme 505 Pincer Nickel(ii)-catalyzed C−h Bond Alkylation O...mentioning

confidence: 99%

3d Transition Metals for C–H Activation

et al. 2018

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C−H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material sciences, crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these C−H functionalizations required precious 4d or 5d transition metal catalysts. Given the cost-effective and sustainable nature of earth-abundant first row transition metals, the development of less toxic, inexpensive 3d metal catalysts for C−H activation has gained considerable recent momentum as a significantly more environmentally-benign and economically-attractive alternative. Herein, we provide a comprehensive overview on first row transition metal catalysts for C−H activation until summer 2018.

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“…Concurrently, Ackermann group demonstrated the use of O-tethered 2-pyridyl DG for the orthoselective CÀ H acyloxylation using broad range of carboxylic acids under Ru-catalysis employing AgSbF 6 as the additive and K 2 S 2 O 8 as the oxidant. [42] In addition, Shi group [43] reported a copper-catalyzed acyloxylation of benzamides using N,Nbidentate directing group while Miura group [44] utilized the Ru-catalysis for the CÀ H acetoxylation of indole and carbazole scaffolds utilizing Ag 2 CO 3 as the oxidant at elevated temperature (Scheme 9C-D). Later, Li group disclosed a Rhcatalyzed pyridyl-directed strategy for CÀ O bond formation by exploiting various carboxylic acids as the coupling partners in the presence of AgF as the oxidant (Scheme 9E).…”

Section: Acyloxylationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Directing Group Assisted (Hetero)aryl C−H Functionalization: Construction of C−C/C‐Heteroatom Bonds

Sarkar

Shah

Maharana

et al. 2021

The Chemical Record

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Transition-metal-catalyzed CÀ H functionalization is one of the fascinating scientific fronts in organic synthesis for the formation of conjugated arenes and has emerged as a benchmark to revolutionize the synthetic enterprise since past decades. In this realm, chelationguided functionalization of CÀ H bonds using an exogenous directing group has received considerable attention recently for the expedient regioselective construction of CÀ C and Cheteroatom bonds as an efficient and sustainable alternative. This article outlines our contribution towards a wide variety of transformations that have been achieved by the directed CÀ H functionalization through the fine tuning of catalytic systems.

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Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids

Cited by 22 publications

References 27 publications

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

3d Transition Metals for C–H Activation

Transition‐Metal‐Catalyzed Directing Group Assisted (Hetero)aryl C−H Functionalization: Construction of C−C/C‐Heteroatom Bonds

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