Palladium is shown to catalyze an intramolecular aminocyclopropanation of norbornenes with aliphatic vinyl halides in good yields. The reaction tolerates a variety of amine substituents and gives good results with a variety of carbocyclic and oxabicyclic [2.2.1] alkene acceptors. Notably, stabilized enolate nucleophiles were also employed in cyclopropanation reactions.
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http://dx.doi.org/10.1021/ol401383m | DOI Listing |
Org Biomol Chem
January 2025
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.
Herein, we report a Ni-catalyzed cross-electrophile coupling of aryl/vinyl halides with benzothiazolium salts derived from alcohols. Our findings demonstrate that primary alkyl benzothiazolium salts serve as effective C(sp)-O substrates, facilitating coupling with aryl and vinyl halides. This method not only enables the formal functionalization of primary alcohols but also provides experimental support for previously established sequential alcohol halogenation and Ni-catalyzed reductive coupling platforms.
View Article and Find Full Text PDFChem Commun (Camb)
December 2024
Department of Chemistry, School of Pharmacy, Air Force Medical University, Xi'an, 710032, China.
An efficient synthesis of continuously substituted quinoline derivatives palladium-catalyzed intramolecular 6- imidoylative cyclization of -alkenyl aryl isocyanides with (hetero)aryl halides or vinylic triflates has been developed. The reaction proceeds through the concerted metalation-deprotonation (CMD) mechanism by activation of a vinyl C-H bond with imidoylpalladium assisted by the carboxylate.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States.
We disclose a broad platform for copper-catalyzed atom transfer radical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)(OTf) enables radical addition of electron-deficient alkyl halides to acrylates, acrylamides, and vinyl sulfones in fair to excellent yields. The resultant ATRA products can be used in a variety of telescoped reactions, including substitution with basic amine nucleophiles to afford α-amino esters.
View Article and Find Full Text PDFNat Commun
November 2024
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China.
The catalytic asymmetric synthesis of axially chiral alkenes remains a daunting challenge due to the lower rotational barrier, especially for longer stereogenic axis (e.g. C-B axis).
View Article and Find Full Text PDFPrecis Chem
November 2024
Frontiers Science Center for Transformative Molecules (FSCTM), Center for Chemical Glycobiology, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Department of Chemical Biology, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.
Nonclassical -glycosides, distinguished by their unique glycosidic bond connection mode, represent a promising avenue for the development of carbohydrate-based drugs. However, the accessibility of nonclassical -glycosides hinders broader investigations into their structural features and modes of action. Herein, we present the first example of Pd-catalyzed stereospecific glycosylation of nonclassical anomeric stannanes with aryl or vinyl halides.
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