The importance of nitrogen-containing compounds as synthetic intermediates and biologically active agents has created the need for practical and general amination procedures. The goal of the proposed research is to develop such a method. Proposed in Specific Aim 1 is a late transition metal-catalyzed amination reaction of unfunctionalized olefins. This approach involves the addition of nitrile nucleophiles to 1-alkenes to form a variety of highly functionalized products, such as amides, secondary amines, and nitrogen heterocycles. These types of amine subunits are prevalent in top-selling drugs and biologically important compounds. As illustrated in Aim 2, this methodology will ultimately be extended to the corresponding asymmetric process, which in turn, would grant access to enantioenriched 1-chiral amines from inexpensive starting materials. Finally, the proposed research described in both Specific Aims has significant implications in drug development in academic and industrial settings.

Public Health Relevance

Nitrogen-containing compounds, or amines, are found in every major class of medicinal drugs. Despite their importance, general and practical methods to synthesize amines from inexpensive and widely available starting materials remain scarce. The goal of the proposed research is to develop such a method.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32GM099202-02
Application #
8331720
Study Section
Special Emphasis Panel (ZRG1-F04A-G (20))
Program Officer
Fabian, Miles
Project Start
2011-09-12
Project End
2013-08-02
Budget Start
2012-09-12
Budget End
2013-08-02
Support Year
2
Fiscal Year
2012
Total Cost
$47,337
Indirect Cost
Name
Massachusetts Institute of Technology
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
001425594
City
Cambridge
State
MA
Country
United States
Zip Code
02139
DeBergh, J Robb; Niljianskul, Nootaree; Buchwald, Stephen L (2013) Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids. J Am Chem Soc 135:10638-41