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Copper Hydride Catalyzed Anti-Markovnikov Hydration of Olefins

Award Number: F32GM161027
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS
PERIOD OF PERFORMANCE START DATE: 08/16/2026
PERIOD OF PERFORMANCE END DATE: 08/15/2029

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Copper Hydride Catalyzed Anti-Markovnikov Hydration of Olefins - PROJECT SUMMARY/ABSTRACT Efficient and direct methods for the anti-Markovnikov hydration of olefins (adding water across a carbon– carbon double bond) through transition metal mediated catalysis represents an outstanding goal in contemporary synthetic chemistry. Primary alcohols serve as valuable building blocks for synthesizing molecules essential to medicinal, biological, and pharmaceutical domains of research. Contemporary methods to achieve the anti- Markovnikov hydration of olefins requires the stoichiometric use of toxic borane reagents as well as harsh oxidizing peroxides, which limits its applicability towards functionalized substrates. This proposal seeks to discover and develop a catalytic methodology for the anti-Markovnikov hydration of an olefin, facilitated through copper hydride (Cu–H) catalysis. Cu–H catalysis has successfully enabled robust reactivity towards the amination and alkylation of olefins, extending this technology towards hydration however remains challenging. The proposed research looks to develop a discovery platform capable of leveraging Cu–H catalysis to directly access C(sp3)–OH bonds in a regioselective fashion. The proposed research will also aim to discover and further modify nitropyridine oxidants to facilitate robust hydroxylation of our Cu catalyst. The methodology developed in this proposal will be applied towards the synthesis of active pharmaceutical ingredients, further refining and optimizing the reaction platform for broad applications. This work will provide a technology platform capable of accessing valuable primary alcohols of interest to both pharmaceutical and academic areas of research. The Buchwald laboratory at the Massachusetts Institute of Technology (MIT) provides an optimal environment for the proposed research and training. The Buchwald lab has been at the forefront of pioneering novel reactivity through transition metal-catalyzed cross-couplings, specifically towards Cu–H reaction development and discovery. As a member of this lab, I will develop my skills in reaction discovery and reagent design, with a particular focus on uncovering novel reactivity within the realm of anti-Markovnikov olefin hydration chemistry. The synthetic chemistry training I receive through this proposal will complement my current skill set and prepare me for an independent academic career, focusing on novel reaction development facilitated through data science predictive platforms.


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 = $76,300 )
2026	2026	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	001	1	7/24/2026	NEW	$0
2026	2026	MASSACHUSETTS INSTITUTE OF TECHNOLOGY	77 MASSACHUSETTS AVE	CAMBRIDGE	MA	02139	MIDDLESEX	USA	Biomedical Research and Research Training	000	1	7/24/2026	NEW	$76,300
														Subtotal = $76,300

Grand Total All Awards = $76,300

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Copper Hydride Catalyzed Anti-Markovnikov Hydration of Olefins

Award Number: F32GM161027

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS

PERIOD OF PERFORMANCE START DATE: 08/16/2026

PERIOD OF PERFORMANCE END DATE: 08/15/2029

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