Stereoselective Radical Processes for C-H Alkylation and Amination
C-H 烷基化和胺化的立体选择性自由基过程
基本信息
- 批准号:10796195
- 负责人:
- 金额:$ 16.69万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2020
- 资助国家:美国
- 起止时间:2020-04-01 至 2025-02-28
- 项目状态:未结题
- 来源:
- 关键词:AlkylationAmidesAminationAzidesBenignBiologicalBiologyCatalysisCobaltComplexDevelopmentEnvironmentExhibitsHydrogen BondingIsomerismLigandsMedicineMetalsMethodologyMethodsNatural ProductsOpticsOrganic SynthesisPorphyrinsProcessReactionReagentResearch Project GrantsSourceSystemTransition Elementscarbenecatalystchemical reactionchiral moleculecost effectivedesigndiazo compoundenantiomernitrenetool
项目摘要
PROJECT SUMMARY/ABSTRACT
Catalytic Radical Processes for Stereoselective C–H Alkylation and Amination
Chiral molecules are of central importance in biology and medicine. The development of synthetic
methodologies that allow for selective conversion of omnipresent C–H bonds into optically active
compounds while installing various functionalities promises to transform the art and practice of organic
synthesis and should lead to many new applications. Among different approaches, asymmetric C–H
alkylation/amination via metal-catalyzed carbene/nitrene insertion represents one of the most attractive
methods for enantioselective functionalization of C–H bonds. This type of catalytic carbene/nitrene
transfer process provides a direct and general approach for the functionalization of C–H bonds in
organic compounds through stereoselective C–C/C–N bond formation. It serves as a useful tool for the
design and synthesis of biologically and pharmaceutically important chiral organic molecules. While
considerable progress has been made for C–H alkylation and amination by existing catalytic systems
with the use of certain type of diazo compounds as carbene sources and ArI=NTs as nitrene sources,
important challenges remain in the field that validate the need to identify more effective carbene and
nitrene sources in conjunction with the development of fundamentally new metal catalysts for C–H
alkylation and amination.
Guided by the concept of metalloradical catalysis (MRC), this research project is directed toward
the development of new catalytic systems for stereoselective C–H alkylation and amination reactions.
As stable metalloradicals, cobalt(II) complexes of porphyrins [Co(Por)] have been shown to function as
a unique class of catalysts for C–H alkylation and amination through stepwise radical mechanism.
Supported by porphyrin ligands bearing amide functionalities, the Co(II)-based MRC has been shown to
be particularly effective in activating different classes of diazo reagents and organic azides for radical
alkylation and amination of diverse types of C–H bonds, leading to C–C and C–N bond formation with
effective control of reactivity and selectivity. In this proposal, we will focus on the utilization of cobalt(II)
complexes of chiral amidoporphyrins [Co(II)(Por*)] as chiral metalloradical catalysts to advance
enantioselective C–H alkylation and amination reactions for stereoselective synthesis of optically active
organic molecules, including biologically important carbocycles and N-heterocycles.
We hope these studies will ultimately lead to the development of Co(II)-based new catalytic
systems for stereoselective C–H alkylation and amination reactions that can be generally applied
toward practical synthesis of biologically important natural products and pharmaceutically interesting
compounds.
项目总结/文摘
项目成果
期刊论文数量(4)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
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{{ truncateString('X. Peter ZHANG', 18)}}的其他基金
Stereoselective Radical Processes for C-H Alkylation and Amination
C-H 烷基化和胺化的立体选择性自由基过程
- 批准号:
10357917 - 财政年份:2020
- 资助金额:
$ 16.69万 - 项目类别:
Stereoselective Radical Processes for C-H Alkylation and Amination
C-H 烷基化和胺化的立体选择性自由基过程
- 批准号:
10557084 - 财政年份:2020
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
9543478 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
10587778 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
10475223 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
10018889 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
10248461 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
8887619 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
Catalytic Processes for Stereoselective Radical Cyclization Reactions
立体选择性自由基环化反应的催化过程
- 批准号:
9127979 - 财政年份:2015
- 资助金额:
$ 16.69万 - 项目类别:
New Catalytic Systems for Stereoselective C-H Amination
用于立体选择性 C-H 胺化的新型催化系统
- 批准号:
9188930 - 财政年份:2012
- 资助金额:
$ 16.69万 - 项目类别:
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