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Synthesis and Reactions of Carbene Boranes

卡宾硼烷的合成与反应

基本信息

批准号：
1660927
负责人：
Dennis Curran
金额：
$ 30万
依托单位：
University of Pittsburgh
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2017
资助国家：
美国
起止时间：
2017-08-01 至 2019-07-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1660927&HistoricalAwards=false
关键词：
Synthesis Reactions Carbene Boranes

项目摘要

Project SummaryIn this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Dennis P. Curran of the Department of Chemistry at University of Pittsburgh will explore objectives in small molecule synthesis, polymer synthesis, and main group chemistry. The concepts and methods of this work deepen and broaden the disciplines of small molecule synthesis and help in the quest to provide the molecules, materials, and technologies that other disciplines rely on to progress. This is being accomplished with a broad focus on sustainable chemistry by using the common second row element boron (readily available, not toxic, and recyclable) to replace the rare, expensive and/or toxic elements typically employed to drive new reaction discovery. The program is characterized by a strong coupling between advancing the frontiers of science and teaching and training a diverse group of undergraduate students and graduate students. These students move into the workplace to become the human capital that drives progress in many areas that are vital to the health of our citizenry and the economy of our nation. The project also regularly uses cutting edge technology like videoconferences to manage intercontinental collaborations. These collaborations expand the direct teaching/training impact of the proposal beyond Pittsburgh to France, Japan and Scotland.The main focus of this proposal is the development of new boron based methods for synthesis. Much of the work centers on the newly discovered double hydroboration reaction of electron poor alkynes by N-heterocyclic carbene boranes (NHC-boranes). The reactions afford strained boriranes (boracyclopropanes) and an opportunity to discover new, sustainable pathways for the construction of functionalized organic molecules. The scope and mechanism of this unusual new reaction is being studied along with the chemistry needed to replace the NHC-borane group in the product with carbon-carbon and carbon-oxygen bonds. In addition, work toward the development of NIH-difluoroboranes is being pursued in connection with the opportunities for new bond formation that these intermediates afford.

项目摘要在这个由化学系化学合成项目资助的项目中，匹兹堡大学化学系的Dennis P. Curran教授将探索小分子合成，聚合物合成和主族化学的目标。这项工作的概念和方法深化和拓宽了小分子合成的学科，并有助于寻求提供其他学科所依赖的分子，材料和技术。这是通过使用常见的第二行元素硼（容易获得，无毒，可回收）来取代通常用于驱动新反应发现的稀有，昂贵和/或有毒元素，从而广泛关注可持续化学来实现的。该计划的特点是推进科学前沿与教学和培养多样化的本科生和研究生群体之间的强耦合。这些学生进入工作场所，成为推动许多领域进步的人力资本，这些领域对我们公民的健康和我们国家的经济至关重要。该项目还经常使用视频会议等尖端技术来管理洲际合作。这些合作将该提案的直接教学/培训影响从匹兹堡扩展到法国、日本和苏格兰。该提案的主要重点是开发新的硼基合成方法。近年来，人们发现了贫电子炔与N-杂环卡宾硼烷（NHC-硼烷）的双硼氢化反应。这些反应提供了应变boriranes（boracyclopropanes）和一个机会，发现新的，可持续的途径，用于建设功能化的有机分子。这种不寻常的新反应的范围和机理正在沿着用碳-碳和碳-氧键取代产物中的NHC-硼烷基团所需的化学物质进行研究。此外，NIH-二氟硼烷的开发工作正在进行，这些中间体提供了新的键形成的机会。

项目成果

期刊论文数量（15）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates

DOI：
10.1021/jacs.9b05547
发表时间：
2019-08-07
期刊：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
影响因子：
15
作者：
Dai, Wen;Geib, Steven J.;Curran, Dennis P.
通讯作者：
Curran, Dennis P.

Generation and Structure of Unique Boriranyl Radicals

DOI：
10.1021/jacs.7b10788
发表时间：
2017-11-22
期刊：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
影响因子：
15
作者：
Walton, John C.;McFadden, Timothy R.;Curran, Dennis P.
通讯作者：
Curran, Dennis P.

Tris(trimethylsilyl)silane-mediated Reductive Decyanation and Cyano Transfer Reactions of Malononitriles

三(三甲基硅基)硅烷介导的丙二腈还原脱氰化和氰基转移反应

DOI：
10.1246/cl.171231
发表时间：
2018
期刊：
Chemistry Letters
影响因子：
1.6
作者：
Kawamoto, Takuji;Shimaya, Yudai;Curran, Dennis P.;Kamimura, Akio
通讯作者：
Kamimura, Akio

Synthesis and characterization of N-heterocyclic carbene complexes of 1,3,2-dioxaborolane-4,5-dione (NHC-boryl oxalates)

DOI：
10.1016/j.tet.2018.10.031
发表时间：
2018-12
期刊：
Tetrahedron
影响因子：
2.1
作者：
D. Bolt;Steven J. Geib;D. Curran
通讯作者：
D. Bolt;Steven J. Geib;D. Curran

Synthesis, Structure, and Acidity Constants of Ligated α-Boryl Acetic Acids

连接α-硼基乙酸的合成、结构和酸度常数

DOI：
10.1002/chem.201705754
发表时间：
2018
期刊：
Chemistry - A European Journal
影响因子：
0
作者：
Allen, Thomas H.;Horner, Anthony R.;Geib, Steven J.;Weber, Stephen G.;Curran, Dennis P.
通讯作者：
Curran, Dennis P.