We report a Pd-catalyzed β-arylation of cyclic α,β-unsaturated O-methyl oximes with aryl iodides. This reaction shows complete regioselectivity and excellent functional group tolerance. β-Arylation of 2-cyclohexen-1-one O-methyl oxime (existing as 2 : 1 E/Z mixture) with certain aryl iodides such as 4-iodoanisole affords only β-arylated (E)-O-methyl oximes.
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http://dx.doi.org/10.1248/cpb.c19-01012 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Sichuan University, State Key Laboratory of Biotherapy, CHINA.
Herein we report a cobalt-catalyzed hydroglycosylation of terminal alkynes, employing bench-stable ortho-iodobiphenyl (oIB) substituted sulfides as glycosyl donors. This reaction occurs with high stereo- and regioselectivity to afford E-configured vinyl α-C-glycosides, a class of compounds nontrivial to access by previous methods. The use of a bis(oxazoline) ligand with bulky side chains is critical for the high selectivities observed.
View Article and Find Full Text PDFChemistry
January 2025
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991, Moscow, RUSSIAN FEDERATION.
Palladium catalysts form a cornerstone of modern chemistry with upmost scientific and industrial impact. Bulk palladium metal itself is chemically inert, and a sequence of chemical transformations has to be utilized to convert the metal into Pd pre-catalyst covered by ligands. However, the "cocktail" of catalysis concept discovered recently has shown that Pd systems can efficiently operate in catalysis without the necessity of a complicated and expensive pre-installed ligand environment.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Wisconsin─Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Aryl triflates make up a class of aryl electrophiles that are available in a single step from the corresponding phenol. Despite the known reactivity of nickel complexes for aryl C-O bond activation of phenol derivatives, nickel-catalyzed cross-electrophile coupling using aryl triflates has proven challenging. Herein, we report a method to form C(sp)-C(sp) bonds by coupling aryl triflates with alkyl bromides and chlorides using phenanthroline (phen) or pyridine-2,6-bis(-cyanocarboxamidine) (PyBCam)-ligated nickel catalysts.
View Article and Find Full Text PDFOrg Lett
January 2025
College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
The enantioselective synthesis of P(V)-stereogenic compounds has emerged as an interesting research topic primarily due to their significant biological activity and broad application prospects. Herein, we disclose a method for the construction of P(V)-stereogenic compounds from prochiral phosphinamides and aryl iodides via palladium- and chiral norbornene-catalyzed desymmetric annulation. The P(V)-stereogenic compounds were formed with a broad scope with excellent enantiomeric excesses.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.
Carbonylation of aryl electrophiles is an important method for constructing aromatic carbonyl compounds for materials science and pharmaceutical applications. However, there have been few studies on the carbonylation of abundant, inexpensive aryl chlorides. Moreover, the existing carbonylation methods usually require a high temperature, control of the CO pressure, and structurally complex catalysts and ligands.
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