Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids

文献情報

出版日 2023-11-08

DOI 10.1039/D3QO01534C

インパクトファクター 5.281

著者

Junjie Ying, Jingrong Huang, Chenguang Liu, Fa-Jie Chen

原文を見る

要旨

Transition metal-mediated S-arylation has emerged as a powerful tool for the synthesis of S-arylcysteine and S-arylpeptide, which are useful building blocks in pharmacophores and biomolecules. In contrast, the catalytic protocols for arylation remain unexplored, particularly methods employing abundant metal catalysts (e.g. Cu and Ni). Herein, we reported the copper-catalyzed arylation chemistry of S-tosyl peptides with readily available arylboronic acids. This method features excellent yields and a wide variety of aryl groups, enabling the efficient synthesis of S-arylated cysteines and peptides under mild reaction conditions (room temperature, weak base). The reaction can be carried out in both batch and flow, demonstrating its utility in organic synthesis.

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

Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids

文献情報

おすすめジャーナル

関連文献

Probing the electronic and optical properties of silica-coated quantum dots with first-principles calculations

Synthesis of Ge-imogolite: influence of the hydrolysis ratio on the structure of the nanotubes

QM/MM calculation of protein magnetic shielding tensors with generalized hybrid-orbital method: A GIAO approach

Towards understanding the effects of carbon and nitrogen-doped carbon coating on the electrochemical performance of Li4Ti5O12 in lithium ion batteries: a combined experimental and theoretical study

Molecules for organic electronics studied one by one

Theoretical study of the electronically excited radical cations of naphthalene and anthracene as archetypal models for astrophysical observations. Part II. Dynamics consequences‡

Light-induced isomerization dynamics of a cyanine dye in the modulus-controlled regime

Electron-beam evaporated silicon as a top contact for molecular electronic device fabrication

Stabilization of organic field-effect transistors by tert-butyl groups in dibenzotetrathiafulvalene derivatives

Aromaticity in all-metal annular systems: the counter-ion effect

こちらもおすすめ

6-苄基-6,7-二氢-5H-吡咯并3,4-b吡啶とは何ですか？

半硫酸奎宁单水水合物はどのように保存すればよいですか？

D-核糖-5-リン酸二ナトリウムとは何ですか？

異丙基肼はどの業界で使用されていますか？

3-乙酰基-4-羟基喹啉-2(1H)-酮はどのように合成されますか？

Bobcat339はどのように保存すればよいですか？

5-溴-4-甲基-1H-吲唑とは何ですか？

3-(4メトキシフェニル)オキテナン-3カーボイル酸の代替品はありますか？

3-イリドオキシピロロ[2,3-b]ピリジン-5-カルボキシlic酸は安全ですか？

3-氟-4- iodobenolを取り扱う際の実験室安全事項は何ですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

N-(5-Fluoro-2-oxo-2,3-dihydro-4-pyrimidinyl)benzamide

9-(1,1':4',1''-Terphenyl-4-yl)-9H-carbazole

1-(Aminomethyl)cycloheptanol hydrochloride (1:1)

4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

3,3-Dimethylpiperidin-2-one

おすすめサプライヤー