Recent Advances in Catalytic Functionalization of <i>N</i>‐Oxide Compounds <i>via</i> CH Bond Activation

Yan, Guobing; Borah, Arun Jyoti; Yang, Ming‐Hua

doi:10.1002/adsc.201400203

Cited by 130 publications

(41 citation statements)

References 90 publications

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“…[3] In addition, they can behave as Lewis basic directing groups allowing valuable alternative CÀH bond activations and as a consequence, the functionalization of N-oxides is becoming more useful in the synthesis of heterocycles. [4] Therefore, the development of efficient and eco-friendly methodologies for their deoxygenation remains an important goal considering that the major limiatations of the reported procedures for the reduction of heteroaromatic N-oxides are the use of toxic and/or expensive catalysts or reducing agents as well as harsh reaction conditions that many times are unsuitable for functionalized substrates. [5] In addition, the established methods commonly use trivalent phosphorous and boron reagents, or excess of reducing metals as oxygen acceptors, leading to considerable amounts of waste.…”

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confidence: 99%

Molybdenum‐Catalyzed Deoxygenation of Heteroaromatic N‐Oxides and Hydroxides using Pinacol as Reducing Agent

et al. 2017

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A molybdenum-catalyzed deoxygenation of pyridine N-oxides and N-hydroxybenzotriazoles, as well as other azole N-oxides, has been developed using pinacol as an environmentally friendly oxoacceptor. The only by-products are acetone and water making the process a convenient alternative to established protocols in terms of waste generation. The reaction is highly chemoselective and a variety of functional groups are tolerated. The processes are usually very clean allowing the isolation of the pure deoxygenated products after a simple extraction in most cases.

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confidence: 99%

Molybdenum‐Catalyzed Deoxygenation of Heteroaromatic N‐Oxides and Hydroxides using Pinacol as Reducing Agent

et al. 2017

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“…Note that the catalyst retains excellent chemoselectivity towards N−O moieties in the presence of halogens and additional reducible functionalities such carbonyls and cyano groups (Table , Entries 2–3, 6–7). The broad substrate tolerance of the present catalytic system offers an attractive alternative to chemoselectively reduce pyridine and its derivatives, which is known to be a challenging task …”

Section: Resultsmentioning

confidence: 99%

Efficient Chemoselective Reduction of N‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol

Liu

Lohr

et al. 2019

ChemCatChem

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The chemoselective reduction of a wide range of N‐oxides and sulfoxides with alcohols is achieved using a carbon‐supported dioxo‐molybdenum (Mo@C) catalyst. Of the 10 alcohols screened, benzyl alcohol exhibits the highest reduction efficiency. A variety of N‐oxide and both aromatic and aliphatic sulfoxide substrates bearing halogens as well as additional reducible functionalities are efficiently and chemoselectively reduced with benzyl alcohol. Chemoselective N‐oxide reduction is effected even in the presence of potentially competing sulfoxide moieties. In addition, the Mo@C catalyst is air‐ and moisture‐stable, and is easily separated from the reaction mixture and then re‐subjected to reaction conditions over multiple cycles without significant reactivity or selectivity degradation. The high stability and recyclability of the catalyst, paired with its low toxicity and use of earth‐abundant elements makes it an environmentally friendly catalytic system.

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“…Their reactivity has been widely explored, and at present not only the arylation is feasible on a wide range of azine and azole Noxides, but also alkenylation, alkylation, acyloxylation, amination, and sulfonylation involving these interesting synthetic intermediates may be easily carried out [34].…”

Section: Functional Group On Nitrogenmentioning

confidence: 99%

Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides

Bellina

2015

Topics in Organometallic Chemistry

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The direct arylation of heteroaromatic compounds with aryl halides using palladium catalysts has significantly been developed as an effective method for making (hetero)aryl-heteroaryl bonds, which are frequently found in biologically active compounds and functional materials. However, issues regarding costly reagents, regioselectivity, and harsh reaction conditions have to be solved to really compete with the classical transition metal-mediated cross-coupling procedures involving stoichiometric organometallic reagents. In this review, the most relevant developments aimed at solving these issues are summarized

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Recent Advances in Catalytic Functionalization of N‐Oxide Compounds via CH Bond Activation

Cited by 130 publications

References 90 publications

Molybdenum‐Catalyzed Deoxygenation of Heteroaromatic N‐Oxides and Hydroxides using Pinacol as Reducing Agent

Molybdenum‐Catalyzed Deoxygenation of Heteroaromatic N‐Oxides and Hydroxides using Pinacol as Reducing Agent

Efficient Chemoselective Reduction of N‐Oxides and Sulfoxides Using a Carbon‐Supported Molybdenum‐Dioxo Catalyst and Alcohol

Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides

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