Cost-effective synthesis of unsymmetric tetrazines

IF 1.7 4区 化学 Bulletin of the Korean Chemical Society Pub Date : 2024-10-15 DOI:10.1002/bkcs.12903
Jiwon Hwang, Byeongjip Yoon, Sung-Eun Suh
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Abstract

1,2,4,5-Tetrazines serve as versatile two-carbon synthons, essential for synthesizing a variety of (hetero)aromatic compounds. Their specific reactivity with certain dienophiles, without interfering with biochemical processes, makes them ideal for bioorthogonal ligation. Despite their broad utility, current synthetic methods are costly and raise safety concerns, particularly during scale-up. This study introduces safer and more cost-effective synthetic strategies utilizing zinc chloride or boron trifluoride diethyl etherate as catalysts. These alternatives significantly reduce costs and enhance safety, potentially expanding the applicability of tetrazine synthesis across broader research domains.

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经济高效地合成不对称四嗪
1,2,4,5-四嗪是一种多功能的双碳合成物,对于合成各种(杂)芳香族化合物至关重要。它们与某些二烯烃的特异性反应不会干扰生化过程,因此是生物正交连接的理想选择。尽管它们具有广泛的用途,但目前的合成方法成本高昂,且存在安全隐患,尤其是在放大过程中。本研究介绍了利用氯化锌或三氟化硼二乙醚作为催化剂的更安全、更具成本效益的合成策略。这些替代方法大大降低了成本,提高了安全性,有可能将四嗪合成的适用范围扩展到更广泛的研究领域。
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来源期刊
Bulletin of the Korean Chemical Society
Bulletin of the Korean Chemical Society Chemistry-General Chemistry
自引率
23.50%
发文量
182
期刊介绍: The Bulletin of the Korean Chemical Society is an official research journal of the Korean Chemical Society. It was founded in 1980 and reaches out to the chemical community worldwide. It is strictly peer-reviewed and welcomes Accounts, Communications, Articles, and Notes written in English. The scope of the journal covers all major areas of chemistry: analytical chemistry, electrochemistry, industrial chemistry, inorganic chemistry, life-science chemistry, macromolecular chemistry, organic synthesis, non-synthetic organic chemistry, physical chemistry, and materials chemistry.
期刊最新文献
Masthead Cover Picture: Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides (BKCS 10/2024) Jieun Lee, Wooram Lee, Yoseph Kim, Mujin Choi, Seol Ryu, Joonkyung Jang, Youngjo Kim Cost-effective synthesis of unsymmetric tetrazines Moisture-resistant nitroaromatic explosive gas sensor based on hydrophilic pentiptycene polymer Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides
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