有机高价碘化学的研究进展

doi:10.6023/cjoc201605007

有机化学 ›› 2016, Vol. 36 ›› Issue (9): 1973-1984.DOI: 10.6023/cjoc201605007 上一篇下一篇

研究专题

有机高价碘化学的研究进展

段亚南^a, 姜山^a, 韩永超^a, 孙博^a, 张弛^a

a 南开大学元素有机化学国家重点实验室天津化学化工协同创新中心农药国家工程研究中心(天津) 天津 300071

收稿日期:2016-05-07 修回日期:2016-06-11 发布日期:2016-07-07
通讯作者: 张弛 E-mail:zhangchi@nankai.edu.cn
基金资助:
国家自然科学基金（Nos.21472094，21172110，20872064，20572046，21421062，21121002，20421202）、天津市自然科学基金（No.09JCYBJC05900）、高校新世纪优秀人才（No.NCET-07-0461）资助项目.

Recent Advances in Hypervalent Iodine Chemistry

Duan Yanan^a, Jiang Shana^a, Han Yongchao^a, Sun Bo^a, Zhang Chi^a

a State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), National Pesticide Engineering Research Center(Tianjin), Nankai University, Tianjin 300071

Received:2016-05-07 Revised:2016-06-11 Published:2016-07-07
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21472094, 21172110, 20872064, 20572046, 21421062, 21121002, 20421202), the Natural Science Foundation of Tianjin City (No.09JCYBJC05900), and the Program for New Century Excellent Talents in University (No.NCET-07-0461).

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摘要/Abstract

近年来，有机高价碘试剂的反应性研究获得了迅猛的发展.有机高价碘试剂作为高效、多功能化的氧化剂，通常容易制备且操作简单.与已有的合成方法相比，该类试剂参与的反应表现出了许多独特的优点，并且具有与汞、铬、铅、铊等重金属试剂类似的反应性，但却没有这些试剂所带来的毒性和环境污染问题.藉于此，有机高价碘试剂引起了化学合成工作者们越来越多的关注.综述了我们研究小组在有机高价碘化学领域所取得的研究成果，重点介绍了本课题组开发的新试剂和新的试剂组合在若干转化中的优异表现和独特应用，其中包括下述三个方面：（1）可回收型三价碘试剂iodosodilactone在直接成酯、成酰胺及成肽反应中的首次应用以及由活性更高的iodosodilactone类试剂对-（3，5-双三氟甲基苯基）亚碘酰二内酯（FPID）所介导的高效寡肽液相合成方法；（2）新型水溶性五价碘试剂5-三甲铵基邻碘酰苯甲酸内盐（AIBX）的设计、合成及其反应性探索；（3）对三价碘试剂二氯亚碘酰苯反应性的系统性研究.

关键词: 有机高价碘试剂, 亚碘酰二内酯, FPID, AIBX, 二氯亚碘酰苯

In recent years, an explosive growth of reactivities of hypervalent iodine reagents has witnessed and these reagents, featuring facile availability and easy handleness, offer multiple advantages over establised methods as an efficient multipurpose oxidants, whose reactivities are similar to derivatives of mercury, chromium, lead, thallium and other heavy metals, but without the toxicity and environmental problems of these heavy metal agents. Thus, hypervalent iodine reagents have received much more attention from the synthetic chemists. This account mainly summarizes our recent research progress in the area of hypervalent iodine chemistry, especially focusing on the excellent performances and unique applications brought about by the new hypervalent iodine reagents and new combinations of them both developed in our group:(1) first utilization of a recyclable iodine(Ⅲ) reagent iodosodilactone for the direct esterification, amidation and peptide synthesis and high efficient liquid-phase oligo-peptide synthesis mediated by a more powerful iodosodilactone-type reagent, 6-(3,5-bis-(trifluoro-methyl)phenyl)-1H,4H-2aλ³-ioda-2,3-dioxacyclopenta[hi]indene-1,4-dione (FPID); (2) design, synthesis and reactivity explo-ration of a new water-soluble hypervalent iodine(V) reagent, 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ⁵-benzo[d]-[1,2]iodoxol-1-ol anion (AIBX); (3) systematic studies of reactivities of the first hypervalent iodine(Ⅲ) reagent iodobenzene dichloride.

Key words: hypervalent iodine reagents, iodosodilactone, FPID, AIBX, iodobenzene dichloride

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段亚南, 姜山, 韩永超, 孙博, 张弛. 有机高价碘化学的研究进展[J]. 有机化学, 2016, 36(9): 1973-1984.

Duan Yanan, Jiang Shana, Han Yongchao, Sun Bo, Zhang Chi. Recent Advances in Hypervalent Iodine Chemistry[J]. Chin. J. Org. Chem., 2016, 36(9): 1973-1984.

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有机高价碘化学的研究进展

Recent Advances in Hypervalent Iodine Chemistry

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