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Sadphos as Adaptive Ligands in Asymmetric Palladium Catalysis.
Acc Chem Res
January 2024
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200433, China.
ConspectusPalladium catalysis, as one of the most important strategies in asymmetric synthesis, has continuously attracted the attention of organic chemists. With the development of chiral ligands, increasingly challenging reactions and substantial progress in asymmetric catalysis are being realized.Since 2014, we have focused on exploiting a series of sulfinamide phosphine ligands called "Sadphos," including Ming-Phos, Xu-Phos, Xiao-Phos, Xiang-Phos, TY-Phos, PC-Phos, GF-Phos, and WJ-Phos.
View Article and Find Full Text PDFIntermolecular Enamine Mizoroki-Heck Reactions on a Bio-Derived Scaffold.
J Org Chem
January 2024
Faculty of Medicine and Health, University of New England, Armidale, NSW 2351, Australia.
The intramolecular enamine-Mizoroki-Heck reaction allows for the construction of nitrogen-containing heterocycles, although the related intermolecular version is less known. The reactions of enamines derived from Cyrene were investigated under Mizoroki-Heck conditions. An optimization study was used to identify that 1.
View Article and Find Full Text PDFMizoroki-Heck Macrocyclization Reactions at 1 M Concentration Catalyzed by Sub-nanometric Palladium Clusters.
ChemSusChem
August 2023
Instituto de Tecnología Química (UPV-CSIC), Universidad Politècnica de València Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n, 46022, Valencia, Spain.
The synthesis of cyclized organic compounds with more than ten atoms (macrocycles) is traditionally based on reversible reactions under highly diluted conditions, typically <0.05 M, in order to circumvent the formation of intermolecular products. These reaction conditions severely hamper industrial productivity and the use of solid catalysts.
View Article and Find Full Text PDFTransition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.
Acc Chem Res
April 2019
Department of Chemistry , The University of North Carolina at Chapel Hill, Chapel Hill , North Carolina 27599 , United States.
The catalytic construction of C-C bonds between organohalide or pseudohalide electrophiles and fundamental building blocks such as alkenes, arenes, or CO are widely utilized metal-catalyzed processes. The use of simple, widely available unactivated alkyl halides in these catalytic transformations has significantly lagged behind the use of aryl or vinyl electrophiles. This difference is primarily due to the relative difficulty of activating alkyl halides with transition metals under mild conditions.
View Article and Find Full Text PDFIntermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.
Angew Chem Int Ed Engl
February 2019
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Pd -catalyzed Mizoroki-Heck reactions traditionally exhibit poor reactivity with polysubstituted, unbiased alkenes. Intermolecular reactions with simple, all-carbon tetrasubstituted alkenes are unprecedented. Herein we report that pendant carboxylic acids, combined with bulky monophospine ligands on palladium, can direct the arylation of tri- and tetrasubstituted olefins.
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