A synthetic strategy of 4-benzyl-substituted 1,3-butadiene derivatives through Pd-catalyzed three-component coupling reaction of benzyl chlorides, alkynes, and monosubstituted alkenes is described. This tandem coupling reaction forms a C(sp(3))-C(sp(2)) bond and a C(sp(2))-C(sp(2)) bond sequentially in a single-step operation.
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http://dx.doi.org/10.1021/jo300662x | DOI Listing |
Chem Asian J
November 2024
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100 Shiquan 1st Rd, Sanmin District, Kaohsiung City, 807, Taiwan.
We report a metal additive-free iodine-promoted one-step structural reorganization of ynamide-ynes and simultaneous stereoselective 1,2-diiodination of the migrated alkyne to form stereospecific tetrasubstituted alkenyl diiodo-tethered indoles (E-isomer). Molecular iodine is cost effective, user friendly, less toxic, commercially available, and easy to handle. The key features of the reaction include metal-and additive-free environment, selectivity, structural reorganization, mild reaction conditions, simple workup, and gram-scale synthesis.
View Article and Find Full Text PDFAdv Synth Catal
June 2024
Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States.
-BuNI/KSO mediated transformylation from -anisaldehyde to primary amides is reported. The mechanistic studies suggest the reaction occurs via a single electron transfer pathway. Based on the DFT electronic structure calculations of various reaction pathways, the most plausible mechanism involves the formation of a phenyl radical cation and an arenium ion as the key intermediates.
View Article and Find Full Text PDFFront Chem
October 2020
División de Ciencias Naturales y Exactas, Departamento de Química, Universidad de Guanajuato, Guanajuato, Mexico.
The chemoselective reaction of the - followed by the centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential - /O- bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMPO.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2017
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
While chemoselectivities in Pd -catalyzed coupling reactions are frequently non-intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on Pd that allows for an a priori predictable chemoselective Csp2 -Csp2 coupling at C-Br in preference to C-OTf and C-Cl bonds, regardless of the electronic or steric bias of the substrate. The C-C bond formations are extremely rapid (<5 min at RT) and are catalyzed by an air- and moisture-stable Pd dimer under open-flask conditions.
View Article and Find Full Text PDFSpectrochim Acta A Mol Biomol Spectrosc
May 2015
Chemistry Department, Anadolu University, 26470 Eskişehir, Turkey.
A polymeric potassium complex of p-nitrophenol was synthesized and characterized by analytical and spectroscopic techniques. Molecular structure of the complex was determined by single crystal X-ray diffraction study. X-ray structural data show that crystals contain polymeric K(+) complex of p-nitrophenol.
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