Nickel‐Catalyzed Regioselective C–H Bond Mono‐ and Bis‐Nitration of Aryloxazolines with <i>tert‐</i>Butyl Nitrite as Nitro Source

Wan, Li; Qiao, Kai; Yuan, Xin; Zheng, Ming‐Wei; Fan, Bing-Bing; Di, Zhe Chen; Zhang, Dong; Fang, Zheng; Guo, Kai

doi:10.1002/adsc.201700186

Cited by 33 publications

(13 citation statements)

References 84 publications

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“…Bis‐nitration products can be obtained easily by merely increasing the quantity of TBN. The protocol shows a wide‐range of functional group tolerance and the scale‐up experiment shows practical utility …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…The protocol shows awide-range of functional group tolerance and the scale-up experiment shows practical utility. [99] Functionalized 8-aminoquinolines are important building blocks in synthetic organic chemistry and pharmaceutical compounds. Thus new facile routes for their preparation would be highly valuable.…”

Section: Nitrationmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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“…Based on the above observed results and reported pioneering work, plausible mechanism via SET and radical cross coupling for two times was proposed with 1 a as model. As illustrated in Scheme , firstly, Cu(II) cooperated with 1 a to form complex A along with the left HOAc.…”

Section: Resultsmentioning

confidence: 78%

Copper‐catalyzed C‐H Bis‐nitration of 1‐Naphthylamide Derivatives with tert‐Butyl Nitrite as Nitro Source

Qin

Changjing

et al. 2019

ChemistrySelect

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A simple and atom-economical protocol for bis-nitration of 1naphthylamides was firstly discovered with tert-butyl nitrite (TBN) as nitro source and catalyzed by Cu(OAc) 2 . Assisted by picolinamide direction, the C2,4-H bis-nitration could be achieved with excess amount of TBN at 50°C in HOAc. A radical pathway and single electron transfer process might be involved in the bis-nitration process.[a] Prof. Scheme 1. Regioselective CÀ H mono-and bis-nitration of quinoline and naphthalene amides via SET mechanism.

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“…In 2017, Guo's group developed directing group assisted remote nitration of 2‐aryl oxazoline amides with Ni‐based catalyst, 3.0 equiv. of TBN as the nitro source and the reactions were carried out at 80 °C . Recently, we reported selective C−H mono‐nitration of indolines either at −C 5 or −C 7 position (Figure b) by control of weak interactions or “soft‐forces” .…”

Section: Resultsmentioning

confidence: 99%

C−H Mono‐Nitration of Indolines using tert‐Butyl Nitrite

Bose

Mal

2019

Asian J Org Chem

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Nitration reactions on non-prefunctionalized aromatic or heteroaromatic compounds are generally done under harsh conditions. However, these reactions are nonselective to mono-substitution and often produce a mixture of products. Herein we report a mild mono-nitration reaction on indolines, either at À C 5 or À C 7 positions, with 100% regioselectivity using tert-butyl nitrite. The reactions are carried out in acetonitrile and without any additives except nitrating agent tert-butyl nitrite.

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Nickel‐Catalyzed Regioselective C–H Bond Mono‐ and Bis‐Nitration of Aryloxazolines with tert‐Butyl Nitrite as Nitro Source

Cited by 33 publications

References 84 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Copper‐catalyzed C‐H Bis‐nitration of 1‐Naphthylamide Derivatives with tert‐Butyl Nitrite as Nitro Source

C−H Mono‐Nitration of Indolines using tert‐Butyl Nitrite

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