1201191-58-3Relevant academic research and scientific papers
Transition-metal-free formal sonogashira coupling and α-carbonyl arylation reactions
Prueger, Birgit,Hofmeister, Gretchen E.,Jacobsen, Christian Borch,Alberg, David G.,Nielsen, Martin,Jorgensen, Karl Anker
supporting information; experimental part, p. 3783 - 3790 (2010/07/13)
Transition-metal-free formal Sonogashira coupling and α-carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (SNAr) of β-carbonyl sulfones to electron-deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or α-aryl carbonyl compounds. The development of these reactions is presented and, based on investigations under basic and acidic conditions, mechanisms have been proposed. To develop the formal disclosed that expands the reaction concept. The scope of these reactions is demonstrated for the synthesis of Sonogashira and α-carbonyl arylated products from a range of electron-deficient aryl fluorides with a variety of functional groups and aryl-, heteroaryl-, alkyl-, and alkoxy-substituted sulfone nucleophiles. These transition-metal-free reactions complement the metal-catalyzed versions in terms of substitution patterns, simplicity, and reaction conditions.
An asymmetric organocatalytic approach towards allylic amines and β-keto amino compounds
Jacobsen, Christian Borch,Lykke, Lennart,Monge, David,Nielsen, Martin,Ransborg, Lars Krogager,Jorgensen, Karl Anker
supporting information; scheme or table, p. 6554 - 6556 (2010/04/01)
The enantioselective organocatalysed addition of β-keto benzothiazolesulfones to N-Boc-protected imines, leading to intermediates easily transformed into optically active allylic amines or β-keto amino compounds, is presented. The Royal Society of Chemist
