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An Electrochemical Approach to Amine Synthesis from Nitrogen

Award Number: F32GM151784
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS
PERIOD OF PERFORMANCE START DATE: 08/09/2023
PERIOD OF PERFORMANCE END DATE: 08/08/2026

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An Electrochemical Approach to Amine Synthesis from Nitrogen - Project Summary/Abstract Nitrogen-containing functionalities constitute one of the largest classes within health-relevant small molecules. Therefore, the development of new methods to construct carbon–nitrogen bonds remains paramount among opportunities for innovation in chemical synthesis. The Haber–Bosch process is arguably the most important synthetic catalytic process, wherein atmospheric nitrogen (N2) is reduced to ammonia (NH3) by an iron catalyst under high temperature and pressure. In contrast, nature’s N2 fixation catalysts, nitrogenases, operate at ambient conditions using a bimetallic active site. As such, many well-defined coordination complexes have been developed to study key bond-forming steps in N2 reduction, with the goal of designing more efficient catalysts for the synthesis of ammonia and other value-added compounds. While there has been some success in catalytic N2 silylation to give tris(trialkylsilyl)amines, there are no examples of the analogous catalytic process for amine synthesis through carbon–nitrogen bond-formation from N2. Current strategies for the direct conversion of N2 amines require multistep synthetic sequences of metal–N2 complexes with organic electrophiles and subsequent product release under harsh conditions. To circumvent these limitations, the proposed research employs metallocene-based catalysts to promote proton-coupled electron-transfer pathways for radical functionalization of metal–N2 catalysts. Enabled by a renaissance in organic radical generation, easy access to a suite of abundant olefins, and by exploiting complementary reactivity modes of metal–N2 catalysts, a diverse range of primary, secondary, and aryl amine products can be synthesized. The research plan outlines specific approaches that will deliver fundamental insights into reactions of metal–N2 complexes with organic radicals and metal nitrides, commonly proposed intermediates in N2 reduction, with alkenes. These studies will provide the foundation for the realization of a catalytic synthesis of medicinally relevant functional groups from the most abundant source of nitrogen—N2.


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2025 ( Subtotal = $75,520 )
2025	2025	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	3	8/14/2025	NON-COMPETING CONTINUATION	$75,520
														Subtotal = $75,520

Issue Date FY: 2024 ( Subtotal = $73,828 )
2024	2024	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	2	7/16/2024	NON-COMPETING CONTINUATION	$73,828
														Subtotal = $73,828

Issue Date FY: 2023 ( Subtotal = $68,684 )
2023	2023	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	1	8/9/2023	NEW	$0
2023	2023	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	1	8/9/2023	NEW	$68,684
														Subtotal = $68,684

Grand Total All Awards = $218,032

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An Electrochemical Approach to Amine Synthesis from Nitrogen

Award Number: F32GM151784

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS

PERIOD OF PERFORMANCE START DATE: 08/09/2023

PERIOD OF PERFORMANCE END DATE: 08/08/2026

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