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Catalytic Reductive C-H and C-C Silylation with Silyl Acetals

Award Number: R15GM116031
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: 04/01/2016
PERIOD OF PERFORMANCE END DATE: 08/31/2027

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Catalytic Reductive C-H and C-C Silylation with Silyl Acetals - Project Summary/Abstract Interest in organosilane chemistry has increased rapidly in recent years for biomedical research. Because organosilanes are stable, abundant, and virtually nontoxic, they serve as extremely important synthetic building blocks for preparation of a wide range of biomedically important molecules. Despite the advances in organosilane chemistry, the development of broadly applicable, highly selective silylation of unactivated C–C and C–H bonds remains a significant challenge. The long-term goal of this research is to develop highly efficient synthetic methods for the preparation of high-value synthetic building blocks and bioactive molecules. The objective of this proposal is to expand the scope of organosilicon chemistry directed towards organic synthesis by developing new synthetic tools. This entails a new bond activation catalysis that involves C–H and C–C silylation using a traceless N,O-acetal directing group, as well as controlled catalytic hydrosilylation of dicarboxylic acids. The rationale is that the proposed research will significantly improve our knowledge concerning such catalytic strategies, and it will also offer original approaches to structural motifs including readily functionalizable silicon-containing heterocycles. To accomplish the objective, this research program introduces three innovative synthetic strategies. Specific Aim I: develop catalytic C–H silylation of anilines with a traceless N,O-acetal directing group. The hypothesis for Aim I is that an N,O-acetal directs C–H silylation of anilines. The resulting N,O-acetal directing group can be spontaneously removed upon treatment of nucleophilic addition reactions. Specific Aim II: develop catalytic chemo- and stereoselective hydrosilylation of dicarboxylic acid anhydrides and imides. The hypothesis for Aim II is that iridium catalyst with dihydrosilanes to form a binuclear silylene-bridged iridium dimer enables controlled carbonyl hydrosilylation, differentiating between two carbonyls holding different sterics and electronics within 1,3-dicarboxylic acids. Specific Aim III: develop catalytic C–C silylation of cyclopropanols and cyclopropyl amines. The hypothesis for Aim III is that chiral esters and amides can direct silyl acetal to a hindered carbon of cyclopropanols and and cyclopropyl amines regio-, enantio-, and diastereoselectively, leading to a silicon-bearing tetrasubstituted carbon center. The expected outcome of this work is to establish traceless acetal directed silylation strategies for challenging synthetic problems delineated in Aim I–3 that will overcome current limitations and provide high-value synthetic building blocks, substructural units of biomedically relevant targets, and silicon- containing bioactive molecules. The results will have a significant positive impact because the proposed research will be imminently useful to synthetic community and medicinal chemistry areas, specifically in the discovery and production of new therapeutic agents. Finally, we believe that this research program offers exceptional training for young chemists of the future.


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	2024	UNIVERSITY OF TEXAS AT ARLINGTON	701 S NEDDERMAN DR	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	001	3	10/23/2024	COMPETING CONTINUATION	$1,219
2025	2020	UNIVERSITY OF TEXAS AT ARLINGTON	701 S NEDDERMAN DR	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	000	2	10/23/2024	COMPETING CONTINUATION	-$1,219
														Subtotal = $0

Issue Date FY: 2024 ( Subtotal = $449,248 )
2024	2024	UNIVERSITY OF TEXAS AT ARLINGTON	701 S NEDDERMAN DR	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	000	3	8/21/2024	COMPETING CONTINUATION	$449,248
														Subtotal = $449,248

Issue Date FY: 2023 ( Subtotal = $0 )
2023	2020	THE UNIVERSITY OF TEXAS AT ARLINGTON	701 S. NEDDERMAN DR	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	000	2	3/13/2023	COMPETING CONTINUATION	$0
														Subtotal = $0

Issue Date FY: 2020 ( Subtotal = $448,991 )
2020	2020	UNIVERSITY OF TEXAS AT ARLINGTON	400 S CORN ST	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	002	2	7/22/2020	COMPETING CONTINUATION	$303
2020	2020	UNIVERSITY OF TEXAS AT ARLINGTON	400 S CORN ST	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	000	2	4/10/2020	COMPETING CONTINUATION	$448,991
2020	2016	UNIVERSITY OF TEXAS AT ARLINGTON	400 S CORN ST	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	001	1	7/22/2020	NEW	-$303
														Subtotal = $448,991

Issue Date FY: 2016 ( Subtotal = $424,720 )
2016	2016	UNIVERSITY OF TEXAS AT ARLINGTON	POST OFFICE BOX 19136	ARLINGTON	TX	76019	TARRANT	USA	Biomedical Research and Research Training	000	1	3/21/2016	NEW	$424,720
														Subtotal = $424,720

Grand Total All Awards = $1,322,959

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Catalytic Reductive C-H and C-C Silylation with Silyl Acetals

Award Number: R15GM116031

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: 04/01/2016

PERIOD OF PERFORMANCE END DATE: 08/31/2027

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