159029-70-6Relevant articles and documents
Oxidative functionalisation of alcohols and aldehydes via the merger of oxoammonium cations and photoredox catalysis
Nandi, Jyoti,Ovian, John M,Kelly, Christopher B,Leadbeater, Nicholas E.
, p. 8295 - 8301 (2017)
We present a new paradigm for nitroxyl-mediated processes via the merger of oxoammonium cation-mediated oxidation with visible-light photoredox catalysis. The integration of these two forms of catalysis has been realised for the oxidative amidation of aldehydes, furnishing N-acylated heterocycles. Extension of this process to the oxidative amidation of alcohols via the intermediacy of an aldehyde was successfully pursued, thus proffering a general oxidation platform. The activated amides synthesised here are excellent synthetic handles for acylation.
Decarboxylative sp 3 C-N coupling via dual copper and photoredox catalysis
Liang, Yufan,Zhang, Xiaheng,MacMillan, David W. C.
, p. 83 - 88 (2018/07/24)
Over the past three decades, considerable progress has been made in the development of methods to construct sp 2 carbon-nitrogen (C-N) bonds using palladium, copper or nickel catalysis 1,2 . However, the incorporation of alkyl substrates to form sp 3 C-N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge. This cross-coupling system uses naturally abundant alkyl carboxylic acids and commercially available nitrogen nucleophiles as coupling partners. It is applicable to a wide variety of primary, secondary and tertiary alkyl carboxylic acids (through iodonium activation), as well as a vast array of nitrogen nucleophiles: nitrogen heterocycles, amides, sulfonamides and anilines can undergo C-N coupling to provide N-alkyl products in good to excellent efficiency, at room temperature and on short timescales (five minutes to one hour). We demonstrate that this C-N coupling protocol proceeds with high regioselectivity using substrates that contain several amine groups, and can also be applied to complex drug molecules, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.
Synthesis of Spiro(oxazolidinediones): Spiro-2',3(2H),4'-triones and Spiro-2',4'-dione 1,1-Dioxides
Wrobel, Jay,Dietrich, Arlene
, p. 1823 - 1838 (2007/10/02)
Members of two novel families of spiro(oxazolidinediones) have been prepared.Spiro-2',3(2H),4'-triones (4) were synthesized from the corresponding 1-hydroxy-1-carboethoxyethylisoindol-3-one (7) or (10) or their primary amide
