B(C6F5)3‐Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes

Porwal, Digvijay; Oestreich, Martin

doi:10.1002/ejoc.201600556

Cited by 24 publications

(23 citation statements)

References 39 publications

(21 reference statements)

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“…J. Org. Particularly noteworthy is that a NO 2 group on the sulfoxide was not reduced to a NH 2 group (Table 2, entry 7), despite the fact that B(C 6 F 5 ) 3 /Et 3 SiH was reported to reduce aromatic and aliphatic nitro groups, [23] perhaps because of the temperature and the amount of the hydrosilane used. 2017, 3427-3430 www.eurjoc.org ceeded smoothly (Table 2, entries 4-6).…”

Section: Resultsmentioning

confidence: 99%

“…Chloro-and bromosubstituted sulfoxides afforded corresponding products 2e, 2f, and 2h in moderate to high yields, and these compounds could be used in subsequent structural manipulations such as coupling reactions. Particularly noteworthy is that a NO 2 group on the sulfoxide was not reduced to a NH 2 group (Table 2, entry 7), despite the fact that B(C 6 F 5 ) 3 /Et 3 SiH was reported to reduce aromatic and aliphatic nitro groups, [23] perhaps because of the temperature and the amount of the hydrosilane used. In other words, the S-O bond is more reactive than the N-O bond.…”

Section: Resultsmentioning

confidence: 99%

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B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

et al. 2017

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

et al. 2017

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“…[12] In 2016, a B(C 6 F 5 ) 3 -catalyzed hydrosilane reduction of aromatic and aliphatic nitro compounds to the corresponding amines was reported by Oestreich and co-workers (entry 9). [13] Moreover, Benaglia and co-workers explored a HSiCl 3 -mediated reduction of both aromatic and aliphatic nitro compounds to amines with TEA or DIPEA as additive (entry 10). [14] The ultimate goal of these transformations is to find an excellent catalytic system for the practical synthesis of primary amines from nitro compounds, which can tolerant a variety of sensitive functional groups under mild and environmentally friendly reaction conditions.…”

Section: Reduction Of Nitro Compounds To Primary Amines By Organosilanesmentioning

confidence: 99%

Recent Progress on Reductive Coupling of Nitroarenes by Using Organosilanes as Convenient Reductants

et al. 2020

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Nitroarenes are stable, low-cost, and readily available starting materials. The directly utilize nitroarenes in synthetically valuable CÀ N bond formation is of great significance, because the prereduction step to corresponding amines can be avoided. Previously, phosphines and carbon monoxide (CO) are the most widely used reductants in the reductive cyclization or/and carbonylation of nitroarenes. Currently, much attention has been attracted to organosilanes as new potential reducing agents, not only because they are inexpensive, easy-to-handle, and mild reagents, but also various novel reaction models of nitroarenes have been explored. In this review, we mainly summarize the recent progress on the reductive coupling of nitroarenes by using organosilanes as the end reductants. We hope that a deep understanding of the reaction model and underlying working mechanism can provide a timely guideline for researchers who are interested in this fantastic area, leading to further exploration of practical and efficient reductive coupling of nitroarenes for CÀ N bond formation and N-heterocycle synthesis. 1. Introduction 2. Reduction of Nitro Compounds to Primary Amines by Organosilanes 3. Fe-Catalyzed Reductive Coupling of Nitroarenes for CÀ N Bond Formation and N-Heterocycle Synthesis 4. Ni-catalyzed Reductive Coupling of Nitroarenes for CÀ N Bond Formation 5. Cu-catalyzed Reductive Coupling of Nitroarenes for CÀ N Bond Formation and N-Heterocycle Synthesis 6. Organophosphorus-Catalyzed Reductive CÀ N Bond Formation and N-Heterocycles Synthesis from Nitroarenes 7. Other Processes Involve Reductive Coupling of Nitro Compounds by Organosilane Reductants 8.

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“…Functionalized aromatic amines are important intermediates in the production of a range of pharmaceuticals, agrochemicals, cosmetics, herbicides, dyes, and polymers Amines can be obtained through the catalytic hydrogenation of the corresponding aromatic nitro compounds by using reducing agents such as hydrosilanes, sodium borohydride, hydrazine derivatives,, formic acid, and molecular hydrogen , . However, selectivity in the targeted reduction of the –NO 2 group in the presence of other reactive function groups (e.g., alkenes, nitriles, esters, and halogen groups) remains a big challenge for the production of aromatic amines .…”

Section: Introductionmentioning

confidence: 99%

Preparation of Well‐Ordered Mesoporous‐Silica‐Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation

et al. 2018

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MCM‐41‐type mesoporous silica (OMS‐IL) was prepared by using an ionic liquid (1‐hexadecyl‐3‐methylimidazolium bromide) as a template. The XRD and TEM results demonstrated that OMS‐IL was more stable than the MCM‐41 material. Ru nanoparticles were supported on OMS‐IL (Ru/OMS‐IL) by impregnating OMS‐IL with a RuCl3 aqueous solution, and the resulting material was used for the selective reduction of nitroarenes. The effects of the components of the catalysts and the reaction conditions on the catalytic behavior of the prepared catalysts were investigated in detail. Ru/OMS‐IL exhibited high catalytic activity and chemoselectivity for the reduction of various substituted nitroarenes to the corresponding aromatic amines in ethanol with hydrazine hydrate as a hydrogen donor under mild conditions. The Ru/OMS‐IL catalysts were highly stable and could easily be recovered by simple filtration over at least six recycling reactions without any observable loss in catalytic performance.

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B(C₆F₅)₃‐Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes

Cited by 24 publications

References 39 publications

B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

Recent Progress on Reductive Coupling of Nitroarenes by Using Organosilanes as Convenient Reductants

Preparation of Well‐Ordered Mesoporous‐Silica‐Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation

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B(C6F5)3‐Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes

Cited by 24 publications

References 39 publications

B(C6F5)3‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

B(C6F5)3‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

Recent Progress on Reductive Coupling of Nitroarenes by Using Organosilanes as Convenient Reductants

Preparation of Well‐Ordered Mesoporous‐Silica‐Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation

Contact Info

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Resources

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B(C₆F₅)₃‐Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes

B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes