Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents

Hirose, Daisuke; Gazvoda, Martin; Košmrlj, Janez; Taniguchi, Tsuyoshi

doi:10.1039/c6sc00308g

Cited by 75 publications

(44 citation statements)

References 54 publications

(37 reference statements)

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“…[ 44 ] As a number of prior reports have already described the preparation of aromatic azo compounds using iron (II) phthalocyanine (Fe(Pc)) as the catalyst. [ 45–49 ] To our knowledge, Fe(Pc) as catalyst has great potential as oxidation catalysts, however, the Fe(Pc) molecule cannot be recycled, resulting in a significant waste and environmental pollution. Against this backdrop, we particularly focus on the cross‐linked surface engineering with respect to the hollow skeleton for the rational design of heterogeneous catalysts in terms of functionalization methods and structure correlated catalysis.…”

Section: Methodsmentioning

confidence: 99%

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

Zhang

Liu

et al. 2020

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Section: Methodsmentioning

confidence: 99%

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

Zhang

Liu

et al. 2020

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“…In addition, the nitrogen chemical shifts are highly sensitive to structural changes, more so than proton and carbon chemical shifts. Although the low natural abundance of 15 N (0.37%) and gyromagnetic ratio (−2.713 × 10 7 rad T −1 s −1 ) make direct observation of the 15 N nuclide difficult, this has been circumvented by inverse‐detected long‐range heteronuclear shift correlation techniques that are nowadays a part of standard NMR instrumental setup and require relatively small amounts of samples and experimental time . For this investigation the 15 N chemical shifts were extracted from standard 1 H– 15 N HMBC spectra with the parameters adjusted for a long‐range 1 H– 15 N coupling constant of 5 Hz.…”

Section: Resultsmentioning

confidence: 99%

¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

Martek

Mihelač

Gazvoda

et al. 2019

Drug Testing and Analysis

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The high frequency of the synthetic cannabinoid receptor agonists (SCRAs) emergence renders this group of new psychoactive compounds particularly demanding in terms of detection, identification, and responding. Without the available reference material, one of the specific problems is differentiation and structure elucidation of constitutional isomers. Herein, we report a simple and efficient flow chart diagram applicable for a rapid nuclear magnetic resonance (NMR) identification and differentiation between azaindoles, 4‐, 5‐, 6‐, and 7‐azaindole, which is a common structural motif of synthetic cannabinoids. The flow chart diagram is based on 1H NMR and 1H–15N NMR spectra, and to prove the concept, it has been tested on 5F‐MDMB‐P7AICA (1). Spectral and analytical data including standard 1D and 2D NMR spectra, gas chromatography−mass spectrometry (GC−MS), Fourier transform infrared−attenuated total reflectant (FTIR−ATR), Raman, melting point, and combustion analysis are provided for compound 1.

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“…The use of DCC as the condensation reagent realizes the decrease of the amount of alcohols. In addition, Mitsunobu reaction is also reliable method [5][6][7][8].…”

Section: Synthesis Of Carboxylic Acid Esters Using Carboxylic Acids Amentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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In this chapter, recent advances in the synthesis of carboxylic acid esters are summarized based on the utilization of carboxylic acids as electrophiles or nucleophiles in reactions. Condensation reagents or catalysts connect the carboxylic acids with the alcohols to afford the corresponding esters, together with the formation of 1 equiv. of H 2 O, in which the carboxylic acids can be regarded as the electrophile. In contrast, the carboxylate ion intermediates derived from the carboxylic acids react with alkyl halides, carbocations, or their equivalents to produce the esters, in which the carboxylate ions from the carboxylic acids can be regarded as the nucleophile. This chapter mainly introduces the recent progress in this field of the formation of esters, based on the classification of the role of carboxylic acids in reactions.

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Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents

Abstract: Catalytic Mitsunobu reactions have been substantially improved based on strict optimization, mechanistic studies and discovery of a new catalyst.

Cited by 75 publications

References 54 publications

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

Recent Advances in the Synthesis of Carboxylic Acid Esters

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Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents

Abstract: Catalytic Mitsunobu reactions have been substantially improved based on strict optimization, mechanistic studies and discovery of a new catalyst.

Cited by 75 publications

References 54 publications

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

Cross‐Linked Surface Engineering to Improve Iron Porphyrin Catalytic Activity

1H−15N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA

Recent Advances in the Synthesis of Carboxylic Acid Esters

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¹H−¹⁵N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA