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PHOTOINDUCED, COPPER-CATALYZED SUBSTITUTION REACTIONS OF ALKYL ELECTROPHILES BY NITROGEN NUCLEOPHILES

Award Number: R01GM109194
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

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PROJECT SUMMARY/ABSTRACT Because a wide array of nitrogen-containing compounds exhibit bioactivity, the development of new methods for the formation of C–N bonds is a central challenge in synthetic organic chemistry. The discovery of catalysts for organic reactions is often desirable, since they can offer advantages from the standpoints of efficiency/economy. This proposal is directed at the discovery of new methods for metal-catalyzed C–N bond formation. Through the use of photoinduced copper catalysis via a radical pathway, we plan to expand the scope of N- alkylations well beyond that provided by SN2 reactions. These coupling reactions are anticipated to proceed under unusually mild conditions, to have broad applicability for the generation of diverse families of nitrogen- containing compounds, and to proceed with good stereoselectivity (when applicable). The research plan also describes mechanistic studies (e.g., isotopic labeling, stereochemical, mass spectrometry, and electron paramagnetic resonance spectroscopy) that will provide insight into the novel reaction pathways of these photoinduced, copper-catalyzed C–N bond-forming reactions. These mechanistic investigations will play an important role in facilitating our reaction-development program, as well as broadening our understanding of fundamental chemical reactivity.


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: 2023 ( Subtotal = -$1,565 )
2023	2021	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	8	11/1/2022	NON-COMPETING CONTINUATION	-$1,565
														Subtotal = -$1,565

Issue Date FY: 2021 ( Subtotal = $432,313 )
2021	2021	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	8	5/14/2021	NON-COMPETING CONTINUATION	$432,313
														Subtotal = $432,313

Issue Date FY: 2020 ( Subtotal = $712,053 )
2020	2020	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	6	5/22/2020	SUPPLEMENT FOR EXPANSION	$224,213
2020	2020	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	7	5/18/2020	NON-COMPETING CONTINUATION	$487,840
														Subtotal = $712,053

Issue Date FY: 2019 ( Subtotal = $598,892 )
2019	2019	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	004	6	5/13/2019	NON-COMPETING CONTINUATION	$543,365
2019	2019	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	5	12/13/2018	SUPPLEMENT FOR EXPANSION	$55,527
2019	2018	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	003	5	5/10/2019	COMPETING CONTINUATION	$1,913
2019	2017	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	002	4	5/10/2019	NON-COMPETING CONTINUATION	-$1,913
2019	2017	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	4	2/10/2019	NON-COMPETING CONTINUATION	$0
														Subtotal = $598,892

Issue Date FY: 2018 ( Subtotal = $432,313 )
2018	2018	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	5	6/21/2018	COMPETING CONTINUATION	$432,313
2018	2017	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	4	6/18/2018	NON-COMPETING CONTINUATION	$0
														Subtotal = $432,313

Issue Date FY: 2017 ( Subtotal = $355,093 )
2017	2017	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	4	6/20/2017	NON-COMPETING CONTINUATION	$35,510
2017	2017	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	4	2/13/2017	NON-COMPETING CONTINUATION	$319,583
														Subtotal = $355,093

Issue Date FY: 2016 ( Subtotal = $330,390 )
2016	2016	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	3	2/9/2016	NON-COMPETING CONTINUATION	$355,093
2016	2015	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	2	12/8/2015	NON-COMPETING CONTINUATION	-$24,703
														Subtotal = $330,390

Issue Date FY: 2015 ( Subtotal = $455,793 )
2015	2015	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	2	2/23/2015	NON-COMPETING CONTINUATION	$455,793
														Subtotal = $455,793

Issue Date FY: 2014 ( Subtotal = $385,679 )
2014	2014	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	001	1	8/15/2014	SUPPLEMENT FOR EXPANSION	$50,337
2014	2014	CALIFORNIA INSTITUTE OF TECHNOLOGY	1200 E CALIFORNIA BLVD	PASADENA	CA	91125	LOS ANGELES	USA	Biomedical Research and Research Training	000	1	5/12/2014	NEW	$335,342
														Subtotal = $385,679

Grand Total All Awards = $3,700,961

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PHOTOINDUCED, COPPER-CATALYZED SUBSTITUTION REACTIONS OF ALKYL ELECTROPHILES BY NITROGEN NUCLEOPHILES

Award Number: R01GM109194

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

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

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