Through the interplay of high-resolution scanning tunneling microscopy (STM) imaging/manipulation and density functional theory (DFT) calculations, we have demonstrated that an unprecedented selective aryl-aryl coupling via direct C-H bond activation can be successfully achieved on Cu(110). These findings present a simple and generalized route for preparing low dimensional carbon nanomaterials.
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http://dx.doi.org/10.1039/c4cc05482b | DOI Listing |
Nat Catal
April 2024
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Constructive functionalization of unstrained aryl-aryl bonds has been a fundamental challenge in organic synthesis due to the inertness of these bonds. Here we report a split cross-coupling strategy that allows two-fold arylation with diverse aryl iodides through cleaving unstrained aryl-aryl bonds of common 2,2'-biphenols. The reaction is catalyzed by a rhodium complex and promoted by a removable phosphinite directing group and an organic reductant.
View Article and Find Full Text PDFOrg Lett
November 2024
School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, 752050, Odisha, India.
A Ni-catalyzed C-N bond activation of 2-pyridylpyridone and 1-(9-alkyl 9-purin-6-yl)pyridin-2(1)-one and coupling with arylboronic acid have been achieved. A unique feature of this reaction is the strategic activation of the bridging C-N bond and replacement of the pyridone unit with aryl groups using nickel catalyzed Suzuki-Miyaura coupling. This provides an exciting new tool to build C-C bonds in the place of pyridones.
View Article and Find Full Text PDFOrg Lett
December 2024
Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia University (South Campus), 24 Zhaojun Road, Hohhot 010030, China.
Novel monophosphine ligands and with a C-P ring were designed and synthesized for the efficient Pd-catalyzed C(sp)-C(sp) Suzuki coupling. With 0.5 mol % Pddba and 2 mol % , aryl halides coupled with alkylboronic acids to give the products in up to 99% yield.
View Article and Find Full Text PDFChem Sci
August 2024
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University Beijing 100084 China http://mascl.group.
There has been a recent upsurge in research aimed at synthesizing inherently chiral molecules devoid of point, axial, planar and helical chiralities. We present herein our design and enantioselective synthesis of a series of inherently chiral macrocycles. These compounds, termed nor-heteracalixaromatics, feature a biaryl bond that replaces one of the aryl-heteroatom-aryl linkages found in classic heteracalix[4]aromatics.
View Article and Find Full Text PDFACS Omega
July 2024
Department of Chemistry and Chemistry Research Center, Laboratories for Advanced Materials, United States Air Force Academy, Colorado Springs, Colorado 80840, United States.
Pentafluoropyridine was used as a molecular building block for the installation of aryl bromides, affording a series of multisubstituted halogenated arenes. This operationally simplistic methodology offers precise regioselectivity, ease of scalability, and high purity. F Nuclear magnetic resonance (NMR) served as a key diagnostic tool for structural characterization, given the sensitivity with various aryl bromine substitutions on the fluorinated pyridine ring.
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