A chemoselective ipso-hydroxylation of arylboronic acids using urea-hydrogen peroxide under catalyst free condition

Gupta, Shipra Sen; Chaudhary, Priyanka; Srivastava, Vandana; Kandasamy, Jeyakumar

doi:10.1016/j.tetlet.2016.04.099

Cited by 77 publications

(38 citation statements)

References 38 publications

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“…[29a] Further substitution patterns were accessible from dibenzofuran‐4‐ol ( 20 ). The starting material for the sequence was obtained in 94 % yield from the corresponding boronic acid 18 by oxidation (Scheme ) . Triflate formation of the phenol yielded compound 19 .…”

Section: Resultsmentioning

confidence: 99%

“…The starting material for the sequence was obtained in 94 % yield from the corresponding boronic acid 18 by oxidation (Scheme 2). [25] Triflate formation of the phenol yielded compound 19. Its subsequent bromination resulted in a 4,8-substitution pattern in 23.…”

Section: Resultsmentioning

confidence: 99%

“…These starting materials are commercially available or e.g. accessible through condensation reactions or by oxidation of the corresponding boronic acids . The use of dibenzofuranols allows for a broad variety of core derivatizations by modification of the hydroxyl moiety and thus selectivity of functionalizations.…”

Section: Introductionmentioning

confidence: 99%

“…accessible through condensation reactions [24] or by oxidation of the corresponding boronic acids. [25] The use of dibenzofuranols allows for a broad variety of core derivatizations by modification of the hydroxyl moiety and thus selectivity of functionalizations. Moreover, we report the bromine or triflateselective mono-substitution of bromo aryl triflates by means of Suzuki-Miyaura reaction (SMR), respectively.…”

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confidence: 99%

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Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

et al. 2018

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Syntheses of 1,2‐, 1,3‐, 1,4‐, 1,8‐, 2,4‐, 3,4‐, 4,8‐, 1,2,4‐, 1,2,8‐ and 1,3,4‐functionalized dibenzofurans in few steps with good to excellent yields starting from dibenzofuran‐1‐ol or ‐4‐ol are presented. These rapidly accessible bi‐ or tri‐functionalized building blocks are of great interest for the synthesis of bioactive substances or functional material development. Furthermore, for intermediates containing both a bromine and a triflate moiety, a selective mono‐substitution by means of Suzuki–Miyaura reaction (SMR) is described.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

et al. 2018

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“…Phenol has been used as a versatile intermediate for the synthesis of complex structural motifs . Besides these, phenol and its derivatives find applications in medicinal chemistry as antioxidants, antiviral, cardioprotective and pro‐oxidant ,. Traditionally, phenols have been prepared via pyrolysis of sodium salt of benzene sulfonic acid, Dow's process, hydrolysis of arene diazonium salt etc .…”

Section: Introductionmentioning

confidence: 99%

Ascorbic Acid as a Highly Efficient Organocatalyst for ipso‐Hydroxylation of Arylboronic Acid

2018

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An effective organocatalyst, ascorbic acid has been successfully applied for the ipso-hydroxylation of arylboronic acid using 30% aqueous H 2 O 2 as oxidant in water at ambient temperature. The methodology proceeds without using any metal catalyst or base and avoids harsh reaction conditions. The protocol is applicable to various electronically diverse arylboronic acid moieties with good to excellent yield.

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Asymmetric Diarylethenes with Oxidized 2‐Alkylbenzothiophen‐3‐yl Units: Chemistry, Fluorescence, and Photoswitching

Uno

Bossi

Konen

et al. 2019

Advanced Optical Materials

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Reversibly photoswitchable diarylethenes (DAEs) with fluorescent closed forms are applied in biology‐ and material science‐related super‐resolution microscopy. Yet, their full photoswitchable capacities remain unrevealed and unexplored. Due to limitations in synthesis, only 1,2‐[bis‐(2‐ethyl‐1‐benzothiophene‐1,1‐dioxide‐3‐yl)]perfluorocyclopentenes with two identical or very similar aryl groups attached to C‐6 and C‐6′ have been prepared so far. DAEs with increased Stokes shifts related to asymmetric structures and the presence of “push–pull” substituents are introduced in the present study, and their switching power is studied. The new “simplified” asymmetric DAEs possess higher cycloreversion quantum yields, but lower emission efficiencies than their known analogs with extended π‐conjugation paths. Fatigue resistance in organic (acetonitrile and methanol) and aqueous solvents is studied, and the performance in reversible saturable optical fluorescence transition (RESOLFT) microscopy is evaluated. The push–pull structures show an outstanding increase in fatigue resistance, compared with a reference (H/H) diarylethene. Fatigue resistances on the order of thousands of cycles have been observed in acetonitrile solutions without exclusion of air oxygen. The structure–property relationships and facile preparation procedures enable rational design of DAEs applicable as photoswitchable fluorescent probes. A new setup and methodology for measuring switching performance of fluorescent DAEs are introduced.

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A chemoselective ipso-hydroxylation of arylboronic acids using urea-hydrogen peroxide under catalyst free condition

Cited by 77 publications

References 38 publications

Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

Rapid Access to Bi‐ and Tri‐Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions

Ascorbic Acid as a Highly Efficient Organocatalyst for ipso‐Hydroxylation of Arylboronic Acid

Asymmetric Diarylethenes with Oxidized 2‐Alkylbenzothiophen‐3‐yl Units: Chemistry, Fluorescence, and Photoswitching

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