研究者が120年前の問題を解決する新化合物を開発(Researchers create new chemical compound to solve 120-year-old problem)

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2024-05-01 ミネソタ大学

研究者が120年前の問題を解決する新化合物を開発(Researchers create new chemical compound to solve 120-year-old problem)
This graphic depicts the chemical compound that the team of chemists was able to discover. Credit: University of Minnesota

ミネソタ大学ツインシティーズの科学工学部の化学者たちは、120年以上科学者を悩ませていた高反応性の化学化合物を初めて作り出しました。この発見は、新しい薬剤治療、より安全な農業製品、そして優れた電子機器の開発につながる可能性があります。ミネソタ大学の研究チームは、特殊な装置を使用し、窒素が満たされた密閉されたグローブボックスで化学反応を実施することに成功しました。このプロジェクトは、有機金属触媒を用いて行われ、多分野の化学者が協力しました。

<関連情報>

ニッケル結合により、これまでアクセスできなかった7-アザ-2,3-インドリンの単離と反応性が可能になった Nickel binding enables isolation and reactivity of previously inaccessible 7-aza-2,3-indolynes

JENNA N. HUMKE, ROMAN G. BELLI, ERIN E. PLASEK, SALLU S. KARGBO, […], AND COURTNEY C. ROBERTS
Science  Published:25 Apr 2024
DOI:https://doi.org/10.1126/science.adi1606

Editor’s summary

How tightly can a carbon-carbon triple bond be confined? With the right driving reactions, it has become straightforward to squeeze the motif into six-membered rings such as benzyne and then reap the benefit of the prompt reactivity promoted by the strain. However, five-membered rings have tended to be too tight a squeeze. Humke et al. now report that coordination by nickel can relieve the strain just enough to stabilize a triple bond in the pentagonal portion of azaindoles. These azaindolyne complexes were crystallographically characterized and reacted with both nucleophiles and electrophiles. —Jake S. Yeston
Abstract

N-Heteroaromatics are key elements of pharmaceuticals, agrochemicals, and materials. N-Heteroarynes provide a scaffold to build these essential molecules but are underused because five-membered N-heteroarynes have been largely inaccessible on account of the strain of a triple bond in that small of a ring. On the basis of principles of metal-ligand interactions that are foundational to organometallic chemistry, in this work we report the stabilization of five-membered N-heteroarynes in the nickel coordination sphere. A series of 1,2-bis(dicyclohexylphosphino)ethane nickel 7-azaindol-2,3-yne complexes were synthesized and characterized crystallographically and spectroscopically. Ambiphilic reactivity of the nickel 7-azaindol-2,3-yne complexes was observed with multiple nucleophilic, electrophilic, and enophilic coupling partners.

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