Flow photolysis of aryldiazoacetates leading to dihydrobenzofurans <i>via</i> intramolecular C–H insertion

Maguire, Anita R.; O’Callaghan, Katie S.; Baumann, Marcus; Lynch, Denis; Collins, Stuart G.

doi:10.1039/d3ob00541k

Cited by 3 publications

(1 citation statement)

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“…, acid or base catalyzed synthesis, 24–26 organocatalysis, 27 salt catalyzed synthesis 28 as well as electrochemical and photochemical synthesis. 29,30 Transition metal (TM)-catalyzed reactions involving the synthesis of dihydrobenzofuran skeletons are one of the most reliable and beneficial methods. 31 In the past years, several synthetic researchers have designed and reported facile methodologies for the efficient synthesis of dihydrobenzofurans.…”

Section: Introductionmentioning

confidence: 99%

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

Ashraf,

Zahoor,

Ali

et al. 2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

Ashraf,

Zahoor,

Ali

et al. 2024

RSC Adv.

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Intramolecular Photochemical C−H Insertions of α‐Diazocarbonyl Compounds

O'Callaghan,

Collins,

Maguire

2024

Eur J Org Chem

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Intramolecular photochemical C–H insertion reactions of α‐diazocarbonyl compounds are powerful synthetic transformations leading to carbon‐carbon bond formation. While there are limitations in the scope of C–H bonds amenable to C–H insertion under photochemical conditions relative to metal catalysed C–H insertions, the benefits of conducting these synthetically powerful transformations in a metal‐free approach offers “green” advantages. Recent advances in technology have revolutionised the potential for use of photochemical transformations in synthesis, including the wavelength control enabled by LEDs and the benefits associated with continuous flow processing which overcome many of the traditional challenges associated with synthetic photochemistry including scale‐up. The potential for telescoping the synthesis of α‐diazocarbonyl compounds and downstream photochemical reactions is clear. This review summarises the development of intramolecular photochemical C–H insertions and highlights the benefits of recent technological advances.

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Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

Mushtaq,

Irfan,

Haq

et al. 2024

Front. Chem.

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2,3-Dihydrobenzofurans are noteworthy scaffolds in organic and medicinal chemistry, constituting the structural framework of many of the varied medicinally active organic compounds. Moreover, a diverse variety of biologically potent natural products also contain this heterocyclic nucleus. Reflecting on the wide biological substantiality of dihydrobenzofurans, several innovative and facile synthetic developments are evolving to achieve these heterocycles. This review summarizes the transition-metal-free, efficient, and novel synthetic pathways toward constructing the dihydrobenzofuran nucleus established after 2020.

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Flow photolysis of aryldiazoacetates leading to dihydrobenzofurans via intramolecular C–H insertion

Abstract: Flow photolysis of aryldiazoacetates 3-5 leads to C–H insertion to form dihydrobenzofurans 6-8 in a metal-free process, using either a medium pressure mercury lamp (250–390 nm) or LEDs (365 nm...

Cited by 3 publications

References 67 publications

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

Intramolecular Photochemical C−H Insertions of α‐Diazocarbonyl Compounds

Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

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