Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.
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http://dx.doi.org/10.1021/jo034122w | DOI Listing |
J Org Chem
January 2025
Department of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng 252059, China.
Multipalladium clusters possess peculiar structures and synergistic effects for reactivity and selectivity. Herein, -symmetric tripalladium clusters (, 0.5 mol %) afford C-regioselective SMCC of 2,4-dibromopyridine with phenylboronic acids or pinacol esters (C:C up to 98:1), in contrast to Pd(OAc) in ligand-free conditions.
View Article and Find Full Text PDFJ Org Chem
August 2024
Institut Parisien de Chimie Moléculaire (IPCM), Faculté des Sciences et Ingénierie, CNRS, Sorbonne Université, 4 Place Jussieu, 75005 Paris, France.
Limonene undergoes a regioselective Pd(II)-catalyzed C(sp)-H/C(sp)-H coupling with acrylic acid esters and amides, α,β-unsaturated ketones, styrenes, and allyl acetate, affording novel 1,3-dienes. DFT computations gave results in accord with the experimental results and allowed for the formulation of a plausible mechanism. The postfunctionalization of one of the coupled products was achieved via a large-scale Sonogashira reaction conducted under micellar catalysis.
View Article and Find Full Text PDFChem Asian J
August 2024
Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Hangi-cho, Shimogamo, Sakyo-ku, Kyoto, 606-8522, Japan.
In this study, compounds with phenylethynyl (PE) groups introduced at all of the possible positions of the methylene-bridged structure of the 1,1'-bi-2-naphthol backbone (3-PE to 8-PE) were synthesized. Compounds with four or six phenylethynyl groups (3,6-PE, 4,6-PE, 5,6-PE, 6,7-PE, and 3,4,6-PE) were also synthesized. The key reaction for the synthesis of these compounds was the Sonogashira reaction using halogen scaffolds.
View Article and Find Full Text PDFBeilstein J Org Chem
April 2024
Universität Rostock, Institut für Chemie, A.-Einstein-Str.3a, 18059 Rostock, Germany.
The development of a new and straightforward chemoselective method for the synthesis of uracil-based structures by combining Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling is reported. The methodology was applied to synthesize a series of novel compounds. The tolerance of the combination of different functional groups was tested.
View Article and Find Full Text PDFOrg Biomol Chem
May 2024
Institute of Chemistry, Saint Petersburg State University (SPbU), Saint Petersburg, 199034, Russia.
Electrophile-promoted cyclizations of functionalized alkynes offer a useful tool for constructing halogen-substituted heterocycles primed for further derivatization. Preinstallation of an iodo-substituent at the alkyne prior to iodo-cyclization opens access to di-iodinated heterocyclic precursors for the preparation of unsymmetrical heterocycle-fused enediynes. This general approach was used to prepare 2,3-diiodobenzothiophene, 2,3-diiodoindole, and 2,3-diiodobenzofuran, a useful family of substrates for systematic studies of the role of heteroatoms on the regioselectivity of cross-coupling reactions.
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