Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions

Xie, Long‐Yong; Qu, Jie; Peng, Sha; Liu, Kaijian; Wang, Zheng; Ding, Ming‐Wu; Wang, Yi; Cao, Zhong; He, Wei‐Min

doi:10.1039/c7gc03106h

Cited by 132 publications

(43 citation statements)

References 66 publications

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“…Selectfluor 1 is well-known as a powerful fluorination reagent and oxidant, frequently combined with a metal catalyst or photocatalyst in the organic synthesis 61–68 . The N–F breakage of selectfluor resorts to the immigration of external electron from a reductant.…”

Section: Resultsmentioning

confidence: 99%

Visible light-induced direct α C–H functionalization of alcohols

et al. 2019

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Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp3 C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp3 C–H alcohols. The observed reactivity may have significant implications for chemical transformations.

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Section: Resultsmentioning

confidence: 99%

Visible light-induced direct α C–H functionalization of alcohols

et al. 2019

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“…processes, whereas transition‐metal‐free transformations are underrepresented . However, transition‐metal‐mediated/catalyzed reactions are limited in application due to instinctive drawbacks of the catalytic systems . Therefore, the radical cascade cyclization of enynes under transition‐metal‐free conditions have received increasing attention from researchers recently.…”

Section: Methodsmentioning

confidence: 99%

Potassium‐Persulfate‐Promoted Regioselective Azidation/Cyclization of 1,6‐Enynes

Fang²,

Gao

et al. 2019

Asian J Org Chem

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An efficient, environmentally benign and sustainable method for the synthesis of 2-pyrrolidinones from 1,6enynes via an unusual regioselective azidation/cyclization is described. The products have been obtained in good yields without the assistance of any transition-metal catalysts or ligands. To demonstrate the utility of this protocol, the azidation products are converted to a synthetically valuable amine or triazole. This azidation cyclization involves a radical process, allows a regioselective way toward the formation of one CÀ N bond and one CÀ C bond.

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“…2018 年, 何卫民课题组 [42] 2019 年, 袁金伟等 [43] 以 Selectfluor 为氧化剂, 酰胺化合物为氮源, 实现了无过渡金属催化的喹喔啉 2(1H)-酮的直接酰胺化反应(Eq. 17).…”

Section: C-n 偶联unclassified

Selectfluor as “Fluorine-Free” Functional Reagent Applied to Organic Synthesis under Transition Metal-Free Conditions

Kong¹,

Sun²,

Weng³

2020

Chin. J. Org. Chem.

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Selectfluor, a commercial electrophilic fluorination reagent with superior performance, is widely used in fluorination reactions. In recent years, Selectfluor has also been widely applied as "fluorine-free" functional reagent in organic synthesis. Especially the application of Selectfluor/transition metals synergetic catalytic system has made great progress. However, this catalytic system has some disadvantages, such as the use of expensive transition metals and environmental unfriendliness. Therefore, more and more attention has been paid to the application of Selectfluor as "fluorine-free" functional reagent under transition metal-free conditions. In this paper, classified by the type of reactions, the research progress of Selectfluor as a "fluorine-free" functional reagent in organic synthesis under transition metal-free conditions is reviewed, and their future outlook is also discussed.

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Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions

Abstract: A facile, practical and environmentally attractive protocol for the direct diversification of N-heterocycles under ambient, metal- and base-free conditions was developed.

Cited by 132 publications

References 66 publications

Visible light-induced direct α C–H functionalization of alcohols

Visible light-induced direct α C–H functionalization of alcohols

Potassium‐Persulfate‐Promoted Regioselective Azidation/Cyclization of 1,6‐Enynes

Selectfluor as “Fluorine-Free” Functional Reagent Applied to Organic Synthesis under Transition Metal-Free Conditions

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