144493-15-2Relevant articles and documents
Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes
Zhang, Yang,Torker, Sebastian,Sigrist, Michel,Bregovi?, Nikola,Dydio, Pawe?
supporting information, p. 18251 - 18265 (2020/11/02)
Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.
Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: Use of surfactants in cross-coupling reactions
Roberts, Gina M.,Lu, Wenya,Woo, L. Keith
, p. 18960 - 18971 (2015/06/01)
Aqueous Sonogashira coupling between lipophilic terminal alkynes and aryl bromides or iodides gave moderate to high yields at 40°C using readily available and inexpensive surfactants (2.0 w/v% in water) such as SDS and CTAB. The catalyst precursor was 2 m
Improved palladium-catalyzed sonogashira coupling reactions of aryl chlorides
Torborg, Christian,Huang, Jun,Schulz, Thomas,Schaeffner, Benjamin,Zapf, Alexander,Spannenberg, Anke,Borner, Armin,Beller, Matthias
experimental part, p. 1329 - 1336 (2009/08/07)
The improved palladium-catalyzed Sonogashira coupling reactions of aryl chlorides without the necessity to add copper salts were analyzed for the development of palladacycles, adamantylphosphines, carhene ligands, and 2-phosphino-N-arylin-doles and -pyrro