Metal-Free, Visible-Light-Enabled Direct C3–H Arylation of Anthranils

Adak, Tapas; Hu, Chao; Rudolph, Matthias; Li, Jun; Hashmi, A. Stephen K.

doi:10.1021/acs.orglett.0c01999

Cited by 26 publications

(19 citation statements)

References 42 publications

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“…Lei and co‐workers [16i] developed the C−H arylation of isoquinoline, acridine, phthalazine, pyridine, and pyrazine. Their method was applied in the total syntheses of menisporphine and daurioxoisoporphine C. Eosin Y disodium salt [16j] was suitable for direct C−H arylation of anthranils (Scheme 17).…”

Section: C−c Bond Formationmentioning

confidence: 99%

Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts

Zhang

Mei

et al. 2021

Asian J Org Chem

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Aryl diazonium salts are important molecules in organic chemistry. This review discusses advances of their application in light‐mediated reactions summarized in five categories according to the bond formations: (1) C−C formation from alkenes, alkynes, arenes, isocyanide, CO, arylboronic acid, or Grignard reagent. (2–5) C−B, C−N, C−S, and C−P formations. Reactions such as radical addition, elimination, metal‐catalyzed coupling, C−H activation, cyclizations, and rearrangements will be discussed herein.

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Section: C−c Bond Formationmentioning

confidence: 99%

Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts

Zhang

Mei

et al. 2021

Asian J Org Chem

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“…ed the blue LED mediated arylation of benzo[c]isoxazoles (anthranils) with arenediazonium tetrafluoroborates in the presence of eosin Y disodium salt (Scheme 17). 26 This regioselective C-3 arylation of benzo[c]isoxazoles occurs by capturing radicals produced in situ from arenediazonium tetrafluoroborates by 17a. The methodology allows the synthesis of arylated benzo[c]isoxazole derivatives containing halogens, which facilitates the functionalization of the products, operates at room temperature, and is environmentally friendly.…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

Uçar¹,

Daştan²

2021

Synthesis

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Transition-metal-free arylation reactions have attracted considerable attention, because of economic and environmental reasons over the past 40 years. In recent years, in particular, many efforts have been made to develop efficient transition-metal-free approaches for the arylation of heteroarenes. Covering the literature from 2015 to early 2021, this review aims to provide a comprehensive overview of the synthetic and mechanistic aspects of these atom economical and environmentally harmless reactions. 1 Introduction 2 Arylation of Pre-functionalized Heteroarenes 3 Direct C-H Arylation of Heteroarenes 3.1 C(Sp2)-H Arylation 3.2 C(sp3)-H Arylation 4 N-Arylation of Heteroarenes 5 Summary and Outlook

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“… 8 In addition, the Hashmi group disclosed a photoredox C–H arylation of anthranils with aryl diazonium tetrafluoroborates as aryl sources. 9 Despite these advances, the direct oxidative C–H/C–H cross-coupling (also known as cross-dehydrogenative-coupling) 10 of anthranils and simple arenes should be the most straightforward and desirable route to assemble 3-aryl anthranil frameworks by avoiding the use of prefunctionalised aryl sources.…”

Section: Introductionmentioning

confidence: 99%