13529-18-5Relevant academic research and scientific papers
A new paradigm for carbon-carbon bond formation: Aerobic, copper-templated cross-coupling
Villalobos, Janette M.,Srogl, Jiri,Liebeskind, Lanny S.
, p. 15734 - 15735 (2008/09/20)
Thiol esters and boronic acids react to produce ketones under aerobic conditions in the presence of catalytic quantities of a CuI or CuII salt. The reaction occurs at reasonable rates between room temperature and 50 °C at neutral pH using thiol esters derived from bulky 2° amides of thiosalicylamides such as those based on N-tert-butyl-2-mercaptobenzamide. In this mechanistically unprecedented reaction system, the carbon-carbon bond formation occurs through templating of the thiol ester and the boronic acid at copper; the system is rendered catalytic in copper under the aerobic conditions. Copyright
Direct preparation of copper organometallics bearing an aldehyde function via an iodine-copper exchange
Yang, Xiaoyin,Knochel, Paul
, p. 2486 - 2488 (2008/03/28)
The iodine-copper exchange reaction allows the direct preparation of various aryl, heteroaryl and alkenyl cuprates bearing a formyl group, thus allowing a direct synthesis of polyfunctional aldehydes without the need of protecting groups or an additional oxidation step. The Royal Society of Chemistry 2006.
CHEMOSELECTIVE PROTECTION OF HETEROAROMATIC ALDEHYDES AS IMIDAZOLIDINE DERIVATIVES. PREPARATION OF 5-SUBSTITUTED FURAN- AND TIOPHENE-2-CARBOXALDEHYDES VIA METALLO-IMIDAZOLIDINE INTERMEDIATES
Carpenter, Andrew J,,Chadwick, Derek J.
, p. 3803 - 3812 (2007/10/02)
Furan-, tiophene- and N-methylpyrrole-2-carboxaldehydes may be transformed into the corresponding N,N'-dimethylimidazolidines in a reaction not requiring acid catalysis.The resulting furan and tiophene (but not N-methylpyrrole) derivatives may be metallated in high yields and the carboxaldehyde functionality regenerated under very mild conditions.Treatment of the aldehydoketone 2-acetyl-5-formylthiophene with N,N'-dimethylethylenediamine gives only the product of reaction at the aldehyde function thus establishing this methodology as a potentially valuable method for the protection of an aldehyde in the presence of a ketone.
