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Selective C-F Bond Functionalization and Asymmetric Synthesis with Organofluorines

Award Number: R15GM106260
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: 09/10/2013
PERIOD OF PERFORMANCE END DATE: 08/31/2023

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Selective C-F Bond Functionalization and Asymmetric Synthesis with Organofluorines - PROJECT ABSTRACT The ever-increasing demand for synthetic methods that expand currently accessible chemical space and provide efficient access to biologically active compounds has begun to shift attention toward the development of largely unexplored Csp3-F bond functionalization chemistry. Despite considerable progress, in particular with hydrodefluorinations, this task remains quite challenging because the profound electron-withdrawing and stereoelectronic effects of fluorine often interfere with established synthetic protocols and dramatically alter reaction outcomes compared to nonfluorinated analogues. Given the abundance and diversity of readily available fluorinated compounds, the introduction of strategies that provide control over the unique stability and reactivity patterns of the aliphatic carbon-fluorine bond are expected to set the stage for extremely powerful synthetic venues that streamline the production of current and future drugs. The goals of the proposed research are to introduce new Csp3-F bond activation chemistry that is complementary to existing methodologies by enabling unprecedented carbon-carbon and carbon-heteroatom bond formation and an array of new synthetic opportunities with exceptional reaction control, scope and functional group tolerance. The Csp3-F bond, typically considered chemically inert, will become a strategically useful entity representing a latent carbon nucleophile or electrophile, for example via unique Umpolung pathways that allow selective manipulation of orthogonal reactivity modes, with multiple applications including late-stage functionalization. In addition, the Csp3-F bond activation methodology will be extended to catalytic asymmetric cross- coupling chemistry and the (organo)catalytic enantio- and diastereoselective synthesis of a variety of multifunctional organofluorines carrying two contiguous chirality centers from the challenging class of fluoronitriles will be pioneered. While emphasis lies on the development of new synthetic methodologies and asymmetric catalysis, the usefulness of the proposed transformations and reaction products in the total synthesis of biologically active compounds will also be explored. The general feasibility and the synthetic prospects are highlighted with ample proof-of-concept results and mechanistic insights that underscore the broad impact of asymmetric catalysis with fluoronitriles and of strikingly diverse C-F bond functionalization pathways which altogether will exploit organofluorines in currently not possible ways.


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 = $0 )
2025	2020	GEORGETOWN UNIVERSITY	MAIN CAMPUS	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	3	10/15/2024	COMPETING CONTINUATION	$0
														Subtotal = $0

Issue Date FY: 2023 ( Subtotal = $458,705 )
2023	2023	GEORGETOWN UNIVERSITY	MAIN CAMPUS	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	4	7/25/2023	COMPETING CONTINUATION	$458,705
														Subtotal = $458,705

Issue Date FY: 2022 ( Subtotal = $0 )
2022	2020	GEORGETOWN UNIVERSITY	MAIN CAMPUS	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	001	3	10/24/2021	COMPETING CONTINUATION	$47,378
2022	2017	GEORGETOWN UNIVERSITY	MAIN CAMPUS	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	2	10/24/2021	COMPETING CONTINUATION	-$47,378
														Subtotal = $0

Issue Date FY: 2020 ( Subtotal = $422,066 )
2020	2020	GEORGETOWN UNIVERSITY (THE)	37TH AND O ST NW	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	001	3	9/14/2020	COMPETING CONTINUATION	$422,066
2020	2017	GEORGETOWN UNIVERSITY (THE)	37TH AND O ST NW	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	2	9/11/2020	COMPETING CONTINUATION	$0
														Subtotal = $422,066

Issue Date FY: 2018 ( Subtotal = $0 )
2018	2013	GEORGETOWN UNIVERSITY (THE)	37TH & O ST NW	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	1	1/11/2018	NEW	$0
														Subtotal = $0

Issue Date FY: 2017 ( Subtotal = $426,099 )
2017	2017	GEORGETOWN UNIVERSITY (THE)	37TH & O ST NW	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	2	9/6/2017	COMPETING CONTINUATION	$426,099
														Subtotal = $426,099

Issue Date FY: 2013 ( Subtotal = $337,287 )
2013	2013	GEORGETOWN UNIVERSITY	37TH & O STREETS, NW	WASHINGTON	DC	20057	DISTRICT OF COLUMBIA	USA	Biomedical Research and Research Training	000	1	9/10/2013	NEW	$337,287
														Subtotal = $337,287

Grand Total All Awards = $1,644,157

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Selective C-F Bond Functionalization and Asymmetric Synthesis with Organofluorines

Award Number: R15GM106260

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: 09/10/2013

PERIOD OF PERFORMANCE END DATE: 08/31/2023

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