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Catalytic Methods for Organic Synthesis

Award Number: R35GM133326
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)
PERIOD OF PERFORMANCE START DATE: 08/15/2019
PERIOD OF PERFORMANCE END DATE: 06/30/2030

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Catalytic Methods for Organic Synthesis - PROJECT SUMMARY Transition-metal-catalyzed cross-coupling reactions are among the most important methods for the synthesis of pharmaceuticals and enable facile preparation of molecules essential for synthetic chemistry, medicinal chemistry and pharmaceutical purposes. Further advancement in the field of cross-coupling is closely tied to (1) the development of new broadly applicable cross-coupling precursors, and (2) the design of new highly active catalysts that allow rapid access to important pharmaceutically relevant structural motifs. The goal of our research for the next five years is to develop new, highly active, electron-rich, flexible catalysts and NHC-metal (NHC = N-heterocyclic carbene) complexes to access chemical transformations, mechanisms and concepts of high synthetic value that are not readily available or limited by other methods. Over the past five years, the PI’s laboratory has been focused on (1) the development of a new reaction manifold of carboxylic acids that permits rapid access to metal electrophiles from ubiquitous carboxylic acids, and (2) the development of new classes of well-defined metal catalysts based on NHC ligands. In the past five years, the laboratory has developed several new classes of NHC ligands and NHC- metal complexes. These catalysts include (1) sterically-hindered NHC ligands based on aniline peralkylation, (2) rapidly dissociating [Pd(NHC)(µ-Cl)Cl]2 chloro dimer catalysts, (3) well-defined Pd(II)-NHC catalysts bearing anilines as ancillary ligands, (4) unsymmetrical, adjustable and sterically-flexible NHC ligands, (5) sterically- defined biaryl NHC ligands based on imidazo[1,5-a]pyridine-3-ylidene architecture, (6) amino-decorated imidazo[1,5-a]pyridine-3-ylidenes, (7) sterically-hindered N-alkyl NHC ligands, (8) freely-rotatable NHC ligands, (9) abnormal, sterically-differentiated and strongly s-donating 1,2,3-triazol-5-ylidenes, (10) sterically-hindered CAAC ligands, (11) bifunctional NHC ligands. The ligands and catalysts have been commercialized in collaboration with MilliporeSigma to enable broad access of academic and industrial researchers. In the area of carboxylic acid cross-coupling, the PI has developed a series of decarbonylative transformations with a focus on biaryl, heterobiaryl, alkynyl and heteroatom cross-coupling. A collaboration with Pfizer has established the utility of carboxylic acid building blocks in pharmaceutical research. Our studies will outline the synthesis and generation of catalysts that promote a broad range of important processes by controlling elementary steps of the catalytic cycle and processes that are currently beyond the scope of current methods, including functionalization of p-systems and activation of C–F, C–O, C– S and C–N bonds as well as C–C, C–N and C–X cross-coupling reactions that are routinely employed in the most important pharmaceutical transformations. The new catalytic methods and catalysts targeted by our research program will significantly advance the ability of synthetic chemists to develop structural motifs for the construction of bioactive molecules.


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: 2026 ( Subtotal = $414,176 )
2026	2026	RUTGERS, THE STATE UNIVERSITY	123 WASHINGTON ST	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	7	6/18/2026	NON-COMPETING CONTINUATION	$414,176
														Subtotal = $414,176

Issue Date FY: 2025 ( Subtotal = $409,761 )
2025	2025	RUTGERS, THE STATE UNIVERSITY	123 WASHINGTON ST	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	001	6	5/28/2025	COMPETING CONTINUATION	$409,761
2025	2023	RUTGERS, THE STATE UNIVERSITY	123 WASHINGTON ST	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	5	5/6/2025	NON-COMPETING CONTINUATION	$0
														Subtotal = $409,761

Issue Date FY: 2023 ( Subtotal = $378,644 )
2023	2023	RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY	123 WASHINGTON ST STE 510	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	5	5/31/2023	NON-COMPETING CONTINUATION	$378,644
														Subtotal = $378,644

Issue Date FY: 2022 ( Subtotal = $378,644 )
2022	2022	RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY	123 WASHINGTON ST STE 510	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	4	6/15/2022	NON-COMPETING CONTINUATION	$378,644
														Subtotal = $378,644

Issue Date FY: 2021 ( Subtotal = $378,644 )
2021	2021	RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY	123 WASHINGTON ST STE 510	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	3	6/24/2021	NON-COMPETING CONTINUATION	$378,644
														Subtotal = $378,644

Issue Date FY: 2020 ( Subtotal = $376,380 )
2020	2020	RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY	123 WASHINGTON ST STE 510	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	2	5/20/2020	NON-COMPETING CONTINUATION	$376,380
														Subtotal = $376,380

Issue Date FY: 2019 ( Subtotal = $376,380 )
2019	2019	RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY	123 WASHINGTON ST STE 510	NEWARK	NJ	07102	ESSEX	USA	Biomedical Research and Research Training	000	1	8/9/2019	NEW	$376,380
														Subtotal = $376,380

Grand Total All Awards = $2,712,629

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Catalytic Methods for Organic Synthesis

Award Number: R35GM133326

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

PERIOD OF PERFORMANCE START DATE: 08/15/2019

PERIOD OF PERFORMANCE END DATE: 06/30/2030

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