314-11-4Relevant academic research and scientific papers
N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes
Allen, Laura J.,Cabrera, Pablo J.,Lee, Melissa,Sanford, Melanie S.
supporting information, p. 5607 - 5610 (2014/05/06)
This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.
Sterically controlled, palladium-catalyzed intermolecular amination of arenes
Shrestha, Ruja,Mukherjee, Paramita,Tan, Yichen,Litman, Zachary C.,Hartwig, John F.
supporting information, p. 8480 - 8483 (2013/07/19)
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.
