RUI: Development of New Reagents and Synthetic Methodologies Based on Hypervalent Iodine Chemistry

RUI：基于高价碘化学的新试剂和合成方法的开发

基本信息

批准号：
2243793
负责人：
Viktor Zhdankin
金额：
$ 35.73万
依托单位：
University of Minnesota Duluth
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2023
资助国家：
美国
起止时间：
2023-07-01 至 2026-06-30
项目状态：
未结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=2243793&HistoricalAwards=false
关键词：
RUI Development New Reagents Synthetic

项目摘要

With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Viktor V. Zhdankin of the University of Minnesota Duluth (UMD) is studying the development of new reagents and synthetic methodologies based on the organic chemistry of iodine. The project is exploring the preparation and fundamental chemistry of new hypervalent iodine compounds. The ability of hypervalent iodine species to modify organic compounds when coupled with their efficiency and sustainability makes them useful among academic and industrial scientists. This utility is the result of iodine behaving much like a transition metal in many applications. The continued exploration and utilization of these similarities is leading to the development of new useful methodologies for modern organic chemistry. More broadly speaking, this project is at the interface of organic and inorganic chemistry and is well-suited for undergraduate, graduate, and more advanced researchers including researchers in industry. The project is expected to provide high level of education and training for students, many of whom are underrepresented in science. A broad study of new, metal-free, iodine-mediated reactions and an exploratory search for new and potentially useful hypervalent reagents is proposed. Specific objectives include: (i) the development of pseudocyclic arylbenziodoxaboroles as benzyne precursors and highly efficient electrophilic arylating reagents under neutral, aqueous conditions, (ii) the exploration of 4-iodonium substituted arylboronic acids as para-benzyne precursors, (iii) the study of the synthesis and reactivity of stabilized iodonium derivatives of porphyrins and dipyrromethenes, and (iv) the search for new types of polyvalent iodine compounds that are stabilized by internal halogen bonding. New synthetic methodologies based on these efforts will contribute to the discovery of environmentally benign methods for chemical synthesis as they utilize non-toxic iodine compounds in water as catalysts or as recoverable/recyclable reagents. The successful development of this methodology will have an impact on the areas of science where the synthesis of organic molecules is required, such as in academia and in the pharmaceutical, chemical, and agricultural industries.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

在化学合成计划的支持下，明尼苏达大学Duluth大学（UMD）的Viktor V. Zhdankin教授正在研究基于碘的有机化学的新试剂和合成方法的开发。该项目正在探索新的高价值碘化合物的制剂和基本化学。高价值碘物种在其效率和可持续性中修饰有机化合物的能力使它们在学术和工业科学家中有用。该效用是碘在许多应用中的过渡金属的结果。这些相似性的持续探索和利用导致了现代有机化学的新有用方法的发展。从广义上讲，该项目位于有机和无机化学的界面，非常适合本科，研究生以及包括工业研究人员在内的更高级研究人员。预计该项目将为学生提供高水平的教育和培训，其中许多人在科学领域的人数不足。提出了对新的，无金属的碘介导的反应以及对新的且潜在有用的超价试剂进行探索性搜索的广泛研究。具体目标包括：（i）在中性，水性条件下以苯甲基前体和高度有效的亲电芳基试剂的形式发展，（ii）探索4-碘替代芳基硼酸作为para-benzyne的稳定性（III）（IIIII）（IIIII）的研究卟啉和二吡啶甲烯烯的衍生物，以及（iv）寻找通过内部卤素粘结稳定的新型多价碘化合物。基于这些努力的新合成方法将有助于发现化学合成的环境良性方法，因为它们利用水中的无毒碘化合物作为催化剂或可回收/可回收的试剂。这种方法的成功发展将对需要有机分子综合的科学领域产生影响，例如在学术界和制药，化学和农业行业中。这一奖项反映了NSF的法定任务，并通过使用该基金会的知识分子优点和广泛的影响来评估NSF的法定任务，并被认为是值得的。

项目成果

期刊论文数量（5）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

New Isoxazole‐Substituted Aryl Iodides: Metal‐Free Synthesis, Characterization and Catalytic Activity

新型异恶唑取代芳基碘化物：无金属合成、表征和催化活性

DOI：
10.1002/ejoc.202301191
发表时间：
2024
期刊：
European Journal of Organic Chemistry
影响因子：
2.8
作者：
Uttam, Bhawna;Zhdankin, Viktor V.;Kumar, Ravi
通讯作者：
Kumar, Ravi

Peptide coupling using recyclable bicyclic benziodazolone

DOI：
10.1039/d3cc04431a
发表时间：
2023-12-18
期刊：
CHEMICAL COMMUNICATIONS
影响因子：
4.9
作者：
Uehara，Daigo;Adachi，Sota;Saito，Akio
通讯作者：
Saito，Akio

Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides

DOI：
10.1021/acs.orglett.4c00197
发表时间：
2024-02
期刊：
Organic Letters
影响因子：
5.2
作者：
A. Yoshimura;Kim Ngo;I. Mironova;Zachary S Gardner;Gregory T. Rohde;Nami Ogura;Akiharu Ueki;M. Yusubov;Akio Saito;V. Zhdankin
通讯作者：
A. Yoshimura;Kim Ngo;I. Mironova;Zachary S Gardner;Gregory T. Rohde;Nami Ogura;Akiharu Ueki;M. Yusubov;Akio Saito;V. Zhdankin

Recent Progress in Synthetic Applications of Cyclic Hypervalent Iodine(III) Reagents