One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process

文献情報

出版日 2019-11-18

DOI 10.1039/C9QO01115C

インパクトファクター 5.281

著者

Motoki Ito, Arisa Tanaka, Keiju Hatakeyama, Emi Kano, Kazuhiro Higuchi, Shigeo Sugiyama

原文を見る

要旨

This article describes the first application of 2-aminophenylboronates as precursors for benzynes. Utilizing Rh2(HNCOCF3)4 as the catalyst, Rh(II)-nitrene-mediated N–H amination of the starting material triggered a cascade of oxidation/elimination processes resulting in the generation of benzynes, thus providing suitable conditions for a one-pot cycloaddition with azides or furans. The transformation proceeded under acid-, base-, and fluoride-free conditions, below ambient temperature, and was applicable to a range of substrates containing glycoside and nucleoside moieties, as well as silyl-functional groups.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process

文献情報

おすすめジャーナル

関連文献

Facile protocol for the highly regioselective and stereodivergent synthesis of substituted bishomoallylic alcohols from esters

Facile resolution of constrained geometry indenyl-phenoxide ligation

Thermosensitive PNIPAAm cryogel with superfast and stable oscillatory properties

A novel clean catalytic method for waste-free modification of polysaccharides by oxidation

A new type of bromide anion conducting solid

Stereochemistry of contiguous cyclopropane formation from cascade cyclization of a skipped dienyl homoallyl triflate

Block copolymer libraries: modular versatility of the macromolecular Lego® system

Self-assembled arrays of zinc oxide nanoparticles from monolayer films of diblock copolymer micelles

Construction of a protein array on amyloid-like fibrils using co-assembly of designed peptides

Total synthesis of (+)-belactosin A

こちらもおすすめ

環戊烷-1,3-二甲酸甲酯はどのように合成されますか？

4-メトキシ-1,2,3-スチアゼ-3,5-ジオンとは何ですか？

プロスタグランジンA2について「に適用される法規ガイドラインは何ですか？'

4-アミノ-1-ナフタレン sulfonic 酸についての物理化学的性質は何ですか？

N-GlcNAc-生物素を取り扱う際の実験室安全事項は何ですか？

3-アミノメチルフローラノピペリジン-1-カルボニル酸テルブチルエステルとは何ですか？

6-溴-1-甲基-1H-ベンゾ[d][1,2,3]三氮唑はどのように合成されますか？

4-硫代尿苷はどのように合成されますか？

ブレインナトリユリックペプチド32ラットとは何ですか？

1-(3-氮杂啶)-4-羟基哌啶双盐酸盐の物理化学的性質は何ですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

Diisopropylphosphoramidous dichloride

Tetrahydro-2H-pyran

N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide

4-Bromo-1-methylpiperidine

4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile

おすすめサプライヤー