Molybdenum-Promoted Dearomatization Reactions

钼促进的脱芳构化反应

基本信息

  • 批准号:
    1800051
  • 负责人:
  • 金额:
    $ 51.22万
  • 依托单位:
  • 依托单位国家:
    美国
  • 项目类别:
    Standard Grant
  • 财政年份:
    2018
  • 资助国家:
    美国
  • 起止时间:
    2018-07-01 至 2021-06-30
  • 项目状态:
    已结题

项目摘要

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor W. Dean Harman. Professor Harman is a faculty member and current chair in the Department of Chemistry at the University of Virginia. He is developing new methods for the preparation of novel chemical compounds that have the potential to serve as lead compounds for pharmaceutical development. His unique approach exploits the unusual chemical properties that arise when an aromatic ring is complexed to a metal. These unusual chemical properties lead to new chemical reactions that convert the originally flat aromatic ring into a significantly more complex molecule. The presence of the metal allows for introduction of the complexity in a controlled fashion. The invention of the new methods allows for completely new approaches to the synthesis of a variety of interesting and potentially useful molecules. While not part of this proposal. The project lies at the interface of organic, inorganic, and medicinal chemistry. Students work in a fully interdisciplinary research environment on a wide range of problems and become integrated into the scientific community through attendance and presentations at professional meetings, participation in writing peer-reviewed manuscripts, participating in the proposal-writing process, and meeting other scientists. Thus, it is well suited for the education of scientists at all levels. Professor Harman's group is also well positioned to provide the highest level of education and training for students underrepresented in science. Outreach activities involving K-12 students will also be part of the funded project. Finally, collaborations with professors from undergraduate institutions allow these professors greater exposure to current research methods, and expose their students to major research programs. The goal of this work is the development of new methods for the syntheses of novel molecular substances from aromatic molecules. This is being accomplished by leveraging the unique chemical properties of an aromatic molecule that result from its dihapto-coordination to a transition metal. Such action modifies the chemical reactivity of the aromatic substrate, allowing its elaboration into novel organic compounds. Significantly, these dearomatization reactions are leading to new molecules with considerable stereochemical complexity that are well suited for biological evaluation. Previously, heavy metal dearomatization agents derived from osmium, rhenium, and tungsten have been investigated, exploiting their powerful pi-donating abilities. In this work, the PI is exploring the feasibility and practicality of a dihapto-coordinate dearomatization methodology based on a second-row metal. Fundamental chemical features of molybdenum-based aromatic complexes are being investigated and compared to the analogous heavy metal systems. Differences in bond energies, oxidation state stabilities, pi-interactions, tolerance of chemical reagents, cost, and recyclability are ultimately leading to new synthetic opportunities that complement those provided by the heavy metal based systems. The molecular frameworks that are formed through these studies are providing novel architectures that ultimately will be valuable in the development of new biologically active materials. In many cases there are simply no other means for easily obtaining these compounds. Other broader impacts of this work are related to the professional training of graduate and undergraduate students in the areas of Organic, Inorganic, and Organometallic Chemistry. In addition, graduate students develop their mentoring skills by training and collaborating with undergraduate students.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.
化学部化学合成项目支持W. Dean Harman教授的项目。哈曼教授是弗吉尼亚大学化学系的教员和现任系主任。 他正在开发制备新型化合物的新方法,这些化合物有可能作为药物开发的先导化合物。 他独特的方法利用了芳环与金属络合时产生的不寻常的化学性质。这些不寻常的化学性质导致新的化学反应,将原来平坦的芳环转化为明显更复杂的分子。金属的存在允许以受控方式引入复杂性。新方法的发明为合成各种有趣且潜在有用的分子提供了全新的方法。虽然不属于该提案的一部分。该项目位于有机化学、无机化学和药物化学的交叉领域。学生在完全跨学科的研究环境中研究广泛的问题,并通过参加专业会议和演讲、参与撰写同行评审的手稿、参与提案的撰写过程以及与其他科学家会面来融入科学界。 因此,它非常适合各级科学家的教育。 哈曼教授的团队也有能力为科学领域代表性不足的学生提供最高水平的教育和培训。 涉及 K-12 学生的外展活动也将成为资助项目的一部分。 最后,与本科院校教授的合作使这些教授能够更多地接触当前的研究方法,并让他们的学生接触主要的研究项目。这项工作的目标是开发从芳香分子合成新型分子物质的新方法。这是通过利用芳香族分子与过渡金属的二键配位产生的独特化学性质来实现的。这种作用改变了芳香族底物的化学反应性,使其能够加工成新型有机化合物。值得注意的是,这些脱芳构化反应正在产生具有相当大的立体化学复杂性的新分子,非常适合生物学评估。此前,人们已经研究了源自锇、铼和钨的重金属脱芳构剂,利用了它们强大的π供给能力。在这项工作中,PI正在探索基于第二行金属的双键配位脱芳构化方法的可行性和实用性。钼基芳香族配合物的基本化学特征正在研究中,并与类似的重金属系统进行比较。键能、氧化态稳定性、π相互作用、化学试剂耐受性、成本和可回收性方面的差异最终导致新的合成机会,以补充基于重金属的系统所提供的合成机会。 通过这些研究形成的分子框架提供了新颖的结构,最终将在新的生物活性材料的开发中有价值。在许多情况下,根本没有其他方法可以轻松获得这些化合物。这项工作的其他更广泛的影响与有机、无机和有机金属化学领域的研究生和本科生的专业培训有关。此外,研究生通过培训和与本科生合作来发展他们的指导技能。该奖项反映了 NSF 的法定使命,并通过使用基金会的智力价值和更广泛的影响审查标准进行评估,被认为值得支持。

项目成果

期刊论文数量(6)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Molybdenum-Promoted Synthesis of Isoquinuclidines with Bridgehead CF 3 Groups
钼促进桥头 CF 3 基团异奎宁环的合成
  • DOI:
    10.1021/jacs.9b10781
  • 发表时间:
    2019
  • 期刊:
  • 影响因子:
    15
  • 作者:
    Wilde, Justin H.;Smith, Jacob A.;Dickie, Diane A.;Harman, W. Dean
  • 通讯作者:
    Harman, W. Dean
Molybdenum-Promoted Dearomatization of Pyridines
钼促进吡啶的脱芳构化
  • DOI:
    10.1021/acs.organomet.0c00047
  • 发表时间:
    2020
  • 期刊:
  • 影响因子:
    2.8
  • 作者:
    Wilde, Justin H.;Myers, Jeffery T.;Dickie, Diane A.;Harman, W. Dean
  • 通讯作者:
    Harman, W. Dean
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Walter Harman其他文献

Walter Harman的其他文献

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{{ truncateString('Walter Harman', 18)}}的其他基金

MRI: Acquisition of a rapid-throughput NMR spectrometer at the University of Virginia
MRI:在弗吉尼亚大学购买快速通量核磁共振波谱仪
  • 批准号:
    2215062
  • 财政年份:
    2022
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Standard Grant
High-Precision Synthesis and Analysis of Deuterated Cycloalkene Isotopomers
氘代环烯同位素异构体的高精度合成与分析
  • 批准号:
    2100345
  • 财政年份:
    2021
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Standard Grant
Organic Transformations with Dihapto-Coordinated Arene Complexes
双键配位芳烃配合物的有机转化
  • 批准号:
    1152803
  • 财政年份:
    2012
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
Organic Transformations of eta-2-Arene Complexes
eta-2-芳烃配合物的有机转化
  • 批准号:
    0748986
  • 财政年份:
    2008
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
Organic Transformations with Dihapto-Coordinated Arene Complexes
双键配位芳烃配合物的有机转化
  • 批准号:
    0452016
  • 财政年份:
    2005
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
Organic Transformations with h2-Arene Complexes of Rhenium
铼的 h2-芳烃配合物的有机转化
  • 批准号:
    0111558
  • 财政年份:
    2001
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
Organic Transformations of eta-2- Arene Complexes
eta-2-芳烃配合物的有机转化
  • 批准号:
    9807375
  • 财政年份:
    1998
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Standard Grant
Organic Transformations of n2-Arene Complexes
n2-芳烃配合物的有机转化
  • 批准号:
    9509883
  • 财政年份:
    1995
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
NSF Young Investigator: Pi-Base Promoted Activation of Aromatic Molecules
NSF 青年研究员:Pi 基促进芳香分子的活化
  • 批准号:
    9357125
  • 财政年份:
    1993
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant
Organic Transformations with eta2-Arene Complexes
eta2-芳烃配合物的有机转化
  • 批准号:
    9212008
  • 财政年份:
    1992
  • 资助金额:
    $ 51.22万
  • 项目类别:
    Continuing Grant

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大学里同行推广的 LunchChat 应用程序:在用餐时间联系学生以防止/减少孤独感
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