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A straightforward cross-coupling of aryl thioether with aryl bromide with the aid of nickel salt, magnesium, and lithium chloride in tetrahydrofuran at ambient temperature was accomplished. The one-pot reactions proceeded efficiently via C-S bond cleavage to produce the desired biaryls in modest to good yields, avoiding the use of pregenerated or commercial organometallic reagents.
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http://dx.doi.org/10.1021/acs.orglett.3c00518 | DOI Listing |
J Am Chem Soc
September 2025
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
Cross-electrophile coupling (XEC) reactions are considered to be among the most fundamental construction of carbon-carbon bonds in organic chemistry. Traditionally, stoichiometric reductants, including metallic and organic reagents, are required to promote these conversions, resulting in significant waste that contributes to environmental pollution and increased disposal costs. In this study, we report a divided electrochemical synthesis-based cross-coupling platform in which HO is oxidized at the anode surface to generate electrons that produce a lower oxidation state nickel catalyst on the cathode surface, enabling XEC reactions without the need for metallic or organic reagents.
View Article and Find Full Text PDFChem Rec
September 2025
Department of Chemistry, St. Thomas College Palai, Arunapuram P.O., Kottayam, Kerala, 686574, India.
An α-aryl-substituted enantioenriched ketone is a valuable building block for the production of both natural and medicinal compounds. Research into their asymmetric synthesis can be challenging yet rewarding because of the need to control regio-, chemo-, and enantioselectivity carefully. A wide range of catalytic strategies has been developed during the past three decades to gain access to these favored motifs.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
The enantioselective construction of quaternary carbon stereocenters bearing amine functionalities represents a significant challenge in organic synthesis despite their prevalence in pharmaceutically active compounds. Herein, we report a versatile metallaphotoredox platform for the asymmetric incorporation of amine fragments onto quaternary carbons via coupling of alkene-tethered aryl bromides with readily available α-silylamines. This transformation proceeds under mild conditions without requiring organometallic reagents or stoichiometric reductants.
View Article and Find Full Text PDFChem Commun (Camb)
September 2025
School of Physical and Chemical Sciences, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
Unprotected glycosyl sulfinates undergo Ni-mediated cross coupling with a range of aryl iodides and bromides under photoredox conditions to yield aryl -glycosides, predominantly as the β-anomers. Thioglycoside formation is occasionally observed as a competitive side reaction.
View Article and Find Full Text PDFOrg Lett
September 2025
Kaili Catalyst & New Materials Co., LTD, Shaanxi Key Laboratory of Catalytic Materials and Technology, Xi'an 710299, China.
This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)-NHC catalysts demonstrate superior reactivity in chemoselective Suzuki-Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes.
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