Synthesis, Chiral Resolution, and Optical Properties of 2,18‐Dihydoxy‐5,10,15‐trioxa[9]helicene

Sundar, M. Shyam; Klepetářová, Blanka; Bednářová, Lucie; Muller, Gilles

doi:10.1002/ejoc.202001177

Cited by 8 publications

(4 citation statements)

References 55 publications

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“…From 3 mmol-scale reactions, biaryldiols 3ai and 3ak were isolated in 93 and 91% yields, respectively (Scheme a). The biaryldiols were also readily converted to valuable π-conjugated polycyclic benzofurans 8aj – 8am in high yields, showcasing synthetic utility (Scheme b) …”

Section: Resultsmentioning

confidence: 99%

Ru(II)-Catalyzed Deformylative C–C Activation and Carbene Insertion: Empowering Diversity-Oriented Synthesis of Unsymmetrical Biaryldiols and Heterobiaryl Amino Alcohols

Giri,

Singh,

Mondal

et al. 2024

ACS Catal.

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While 1,1′-biaryl diols and amino alcohols are privileged scaffolds, their streamlined catalytic synthesis with unsymmetrical substitution patterns remains a daunting challenge. Herein, we describe a ruthenium(II)-catalyzed synthesis of unsymmetrical 1,1′-biaryl-2,2′-diols via deformylative coupling of ortho-hydroxy aromatic aldehydes with diverse cyclic diazo compounds. The protocol is operationally simple and scalable and involves intriguing C−C bond activation and carbene insertion cascade to produce a range of diversely functionalized biaryldiols in very high yields and regioselectivity. The methodology is also suitable to access heterobiaryl amino alcohols bearing indole motif, applicable in challenging 2-fold C−C activation leading to valuable tetrahydroxy bis-biaryls, and retains efficacy in the site-selective modification of pharmaceutical agents. DFT studies have also been conducted to illustrate the intricacy of this catalytic cycle.

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Section: Resultsmentioning

confidence: 99%

Ru(II)-Catalyzed Deformylative C–C Activation and Carbene Insertion: Empowering Diversity-Oriented Synthesis of Unsymmetrical Biaryldiols and Heterobiaryl Amino Alcohols

Giri,

Singh,

Mondal

et al. 2024

ACS Catal.

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“…Therefore, helicenes or their derivatives have received much interest in wide utilization [2] such as chiral ligands for asymmetric catalysis, [3] liquid crystal molecules, [4] chiral rotors, [5] sensing, [6] self‐assembly [7] and organic electronics [8] . Due to the advantage of furan to increase molecular interaction and charge transporting ability, [9] synthesis of oxygen‐containing helicenes including their opto‐electronic applications have been reported in recent years [6,9a,10] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Bis(naphthofuran)‐Fused [7]Helicene Derivatives

Hashmi

Thongpanchang

2022

Eur J Org Chem

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Novel benzo[1,2‐b:4,3‐b′]dinaphthofuran (oxa[7]helicene) with various substituents in the central ring were designed and successfully synthesized based on the late stage central ring formation strategy from naphthofuranoneby using an efficient McMurry coupling or Friedel‐Crafts acylation. The photochemical properties of helicenes were evaluated by UV‐Visible absorption spectroscopy and fluorescence spectroscopy, while electrochemical behaviour including their energy profile were investigated by cyclic voltammetry and DFT calculations. According to the computational study, substituents on the central ring could influence both electron delocalization and MO distribution of oxa[7]helicenes resulting in the change in charge transporting ability. In comparison to the parent carbo[7]helicene, the furan unit in conjunction with substituents on helical system caused the bathochromic shift with different absorption pattern and exhibited higher fluorescence quantum yield (ϕf up to 0.63). These new materials showed promising characteristics in optoelectronic application.

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“…We recently reported the synthesis of large oxygen-containing functionalized trioxa [9]helicene from the axially chiral furan derivative. [28] Herein, we present the efficient synthesis of dioxa[6]helicene 4 and its derivatives, attempts at resolution of racemic 4 into enantiomers, single-crystal X-ray analysis of racemic 4, and photophysical properties (UV-Vis absorption, fluorescence, cyclic voltammetry) of dioxa[6]helicene 4 and its derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Stereochemical Behavior of Dioxa[6]helicene Derivatives

Sundar

Dračínský

et al. 2021

ChemistrySelect

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We constructed a helically chiral dioxa [6]helicene by assembling simple phenol building blocks by a combination of two simple reactions involving oxidative cross-coupling followed by dehydrative cyclization. X-ray analysis and density functional calculations (DFT) revealed that the compound dioxa [6] helicene has a helical structure that undergoes helical inversion rapidly at room temperature. We were able to detect the presence of resolvable helical isomers of (À )-menthyloxycarbonyl derivative of dioxa[6]helicene by recording 1 H NMR spectra below 0°C. The investigations of photo physical properties by cyclic voltammetry, UV/Vis-and fluorescence properties with the aid of time-dependent DFT calculations were undertaken.

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Synthesis, Chiral Resolution, and Optical Properties of 2,18‐Dihydoxy‐5,10,15‐trioxa[9]helicene

Cited by 8 publications

References 55 publications

Ru(II)-Catalyzed Deformylative C–C Activation and Carbene Insertion: Empowering Diversity-Oriented Synthesis of Unsymmetrical Biaryldiols and Heterobiaryl Amino Alcohols

Ru(II)-Catalyzed Deformylative C–C Activation and Carbene Insertion: Empowering Diversity-Oriented Synthesis of Unsymmetrical Biaryldiols and Heterobiaryl Amino Alcohols

Synthesis and Properties of Bis(naphthofuran)‐Fused [7]Helicene Derivatives

Synthesis and Stereochemical Behavior of Dioxa[6]helicene Derivatives

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