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Synthetic Methods based on Biphilic Phosphorus Catalysts

Award Number: R01GM114547
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: 03/01/2015
PERIOD OF PERFORMANCE END DATE: 04/30/2028

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Synthetic Methods based on Biphilic Phosphorus Catalysts - PROJECT SUMMARY/ABSTRACT Advances in catalytic science and technology enable the preparation of pharmaceutical agents used to treat human disease. This project has the long-term goal of developing a broad class of inexpensive nonmetal catalysts that promote catalytic transformations via formal oxidation state cycling in qualitative analogy to transition metal catalysis. Within this overarching goal, the primary focus of this proposal is the design and application of phosphorus-based catalysts that function in the P(III)⇌P(V) redox couple. While phosphines are well-established in catalysis as spectator ligands for transition metal catalysis and as nucleophilic catalysts, this research describes innovative phosphorus-based catalysts of novel com- position and structure that explore the structural and electronic conditions required to enable new catalyt- ically-relevant reactivity via reversible P(III)⇌P(V) oxidation state cycling. The first major effort is the de- velopment of new methods for activation of amides and stable oxoanions for direct functionalization via P(III)⇌P(V) redox reactivity. The second major effort is the development of phosphine-catalyzed O-atom transfer methods that result in reductive transformations of nitroarene compounds to furnish functional- ized anilines through the formation of new carbon-nitrogen bonds. The third major effort involves the de- velopment of P(III)⇌P(V)-catalyzed O-atom transfer methods that result in reductive N-functionalization of nitroalkanes, including new phosphacyclic structures that express biphilic P(III)⇌P(V) redox reactivity. The proposed research is expected to yield new practical catalytic methods for the construction of phar- macologically-relevant small molecules that meet the challenges of sustainable synthesis, and an im- proved fundamental understanding the interplay between structure and reactivity in the p-block that will underpin future development of nonmetals for atom transfer, bond activation, and catalysis. Taken to- gether, these outcomes will advance nonmetal-based redox catalysis as a powerful modality in pharma- ceutical synthesis.


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 = $447,189 )
2026	2026	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	13	4/21/2026	NON-COMPETING CONTINUATION	$447,189
														Subtotal = $447,189

Issue Date FY: 2025 ( Subtotal = $447,189 )
2025	2025	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	12	4/24/2025	NON-COMPETING CONTINUATION	$447,189
2025	2023	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	10	1/22/2025	NON-COMPETING CONTINUATION	$0
														Subtotal = $447,189

Issue Date FY: 2024 ( Subtotal = $447,189 )
2024	2024	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	11	6/19/2024	COMPETING CONTINUATION	$447,189
														Subtotal = $447,189

Issue Date FY: 2023 ( Subtotal = $490,588 )
2023	2023	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	10	6/22/2023	SUPPLEMENT FOR EXPANSION	$77,538
2023	2023	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	10	2/16/2023	NON-COMPETING CONTINUATION	$413,050
														Subtotal = $490,588

Issue Date FY: 2022 ( Subtotal = $413,050 )
2022	2022	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	9	2/15/2022	NON-COMPETING CONTINUATION	$371,741
2022	2022	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	9	7/1/2022	NON-COMPETING CONTINUATION	$41,309
														Subtotal = $413,050

Issue Date FY: 2021 ( Subtotal = $413,050 )
2021	2021	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	8	2/3/2021	NON-COMPETING CONTINUATION	$413,050
														Subtotal = $413,050

Issue Date FY: 2020 ( Subtotal = $413,050 )
2020	2020	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	7	1/30/2020	COMPETING CONTINUATION	$413,050
2020	2019	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	6	7/23/2020	NON-COMPETING CONTINUATION	$0
														Subtotal = $413,050

Issue Date FY: 2019 ( Subtotal = $232,278 )
2019	2019	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	6	2/15/2019	NON-COMPETING CONTINUATION	$232,278
														Subtotal = $232,278

Issue Date FY: 2018 ( Subtotal = $233,004 )
2018	2018	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	5	2/8/2018	NON-COMPETING CONTINUATION	$209,703
2018	2018	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	5	5/24/2018	NON-COMPETING CONTINUATION	$23,301
														Subtotal = $233,004

Issue Date FY: 2017 ( Subtotal = $233,004 )
2017	2017	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	006	4	6/20/2017	NON-COMPETING CONTINUATION	$23,370
2017	2017	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	002	4	3/2/2017	NON-COMPETING CONTINUATION	$210,325
2017	2016	PENNSYLVANIA STATE UNIVERSITY, THE	201 OLD MAIN	UNIVERSITY PARK	PA	16802	CENTRE	USA	Biomedical Research and Research Training	004	2	4/12/2017	NON-COMPETING CONTINUATION	-$74
2017	2016	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	3	1/14/2017	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$110,848
2017	2016	PENNSYLVANIA STATE UNIVERSITY, THE	201 OLD MAIN	UNIVERSITY PARK	PA	16802	CENTRE	USA	Biomedical Research and Research Training	000	2	1/13/2017	NON-COMPETING CONTINUATION	-$111,465
2017	2016	PENNSYLVANIA STATE UNIVERSITY, THE	201 OLD MAIN	UNIVERSITY PARK	PA	16802	CENTRE	USA	Biomedical Research and Research Training	003	2	4/12/2017	NON-COMPETING CONTINUATION	-$74
2017	2016	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	005	3	4/12/2017	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$74
														Subtotal = $233,004

Issue Date FY: 2016 ( Subtotal = $234,721 )
2016	2016	PENNSYLVANIA STATE UNIVERSITY	110 TECHNOLOGY CENTER BUILDING	UNIVERSITY PARK	PA	16802	CENTRE	USA	Biomedical Research and Research Training	000	2	4/4/2016	NON-COMPETING CONTINUATION	$234,721
														Subtotal = $234,721

Issue Date FY: 2015 ( Subtotal = $234,894 )
2015	2015	PENNSYLVANIA STATE UNIVERSITY	110 TECHNOLOGY CENTER BUILDING	UNIVERSITY PARK	PA	16802	CENTRE	USA	Biomedical Research and Research Training	000	1	2/20/2015	NEW	$234,894
														Subtotal = $234,894

Grand Total All Awards = $4,239,206

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Synthetic Methods based on Biphilic Phosphorus Catalysts

Award Number: R01GM114547

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: 03/01/2015

PERIOD OF PERFORMANCE END DATE: 04/30/2028

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