Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols

Matsukawa, Yuta; Hirashita, T.

doi:10.1055/s-0037-1611698

Cited by 5 publications

(1 citation statement)

References 8 publications

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“…As shown in Scheme 2 , the newly synthesized thiosemicarbazides 1b – e were then nitrosated under acidic conditions and heated at reflux under basic conditions to provide olates 2b – e , which were converted into chlorotetrazolium salts 3b – e by treatment with POCl 3 followed by anion exchange with HBF 4 . Next, 3d – e were reacted with H 2 NOH, purified by acid-base treatment without any column chromatography 14 to produce hydroxyamides 4d – e , and finally oxidized with HNO 3 after acidification using HBF 4 to obtain nitrosotetrazolium salts 5b – e .…”

Section: Table 1 Catalytic Activities Of ...mentioning

confidence: 99%

A Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a para-Substituted Phenyl Group at the 1- or 3-Position from Anilines

Matsukawa,

Hirashita

2024

Synlett

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A simple, economical, and safe method for the synthesis of mesoionic 1,3-diaryltetrazolium derivatives bearing a p-substituted phenyl group at the 1- or 3-position via thiosemicarbazides was established. Such compounds were directly obtained from the corresponding p-substituted anilines instead of aryl isothiocyanates and arylhydrazines. The newly synthesized mesoionic compounds were successfully converted into the corresponding nitrosotetrazolium salts, which were utilized as catalysts for oxidation of an aliphatic alcohol and analyzed by cyclic voltammetry to determine the correlation between the catalytic efficiencies and redox potentials. The proposed method can be widely applied and is valuable for investigating the substituent effects in mesoionic and related compounds.

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Section: Table 1 Catalytic Activities Of ...mentioning

confidence: 99%

A Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a para-Substituted Phenyl Group at the 1- or 3-Position from Anilines

Matsukawa,

Hirashita

2024

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Oxidation and Reduction

Mehrotra¹

2023

Organic Reaction Mechanisms Series

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Palladium‐Catalyzed Selective o‐Bromination of Mesoionic 1,3‐Diphenyltetrazolium‐5‐olate: Switching the Directing Group from Nitrogen to Oxygen

et al. 2021

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Pd-catalyzed bromination of mesoionic 1,3-diphenyltetrazolium-5-olate (1) was developed. In the presence of palladium acetate (5 mol%), N-bromosuccinimide (110 mol%), and ptoluenesulfonic acid (50 mol%) in 1,2-dichloroethane under reflux, olate 1 underwent bromination to give 1-(2-bromophenyl)-3-phenyltetrazolium-5-olate in a moderate yield as the major product, indicating that the 4-nitrogen atom acts as a directing group rather than the negatively charged oxygen atom. The X-ray-suitable crystals of the corresponding palladacycle were isolated from 1-mesityl-3-phentytetrazolium-5-olate and fully characterized. When both the o-positions of the 3phenyl group were occupied by bromine atoms, o-bromination then occurred at the 1-phenyl group with the aid of the olate oxygen.

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Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols

Abstract: A new aerobic oxidation system consisting of Cu(I)I, 2,2'-bipyridine, N-methyl imidazole, and a mesoionic hydroxyamide was developed, with which selective oxidation of a broad range of benzylic alcohols was achieved.

Cited by 5 publications

References 8 publications

A Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a para-Substituted Phenyl Group at the 1- or 3-Position from Anilines

A Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a para-Substituted Phenyl Group at the 1- or 3-Position from Anilines

Oxidation and Reduction

Palladium‐Catalyzed Selective o‐Bromination of Mesoionic 1,3‐Diphenyltetrazolium‐5‐olate: Switching the Directing Group from Nitrogen to Oxygen

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