A practical nickel-catalyzed decarboxylative cross-coupling of -hydroxyphthalimide esters with 1,4-diiodobenzene analogues has been developed. Under mild reaction conditions, a series of structurally interesting 1,4-dialkylbenzene analogues have been accessed with good functional group tolerance, which are versatile precursors for organic synthesis and a kind of important unit for bioactive molecules, polymers, and other materials. The synthetic application of this methodology was demonstrated by the synthesis of 3-6-dialkylcarbazole derivatives.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.4c02371 | DOI Listing |
J Org Chem
December 2024
College of Sciences, Tianjin University of Science & Technology, Tianjin 300457, P. R. China.
A practical nickel-catalyzed decarboxylative cross-coupling of -hydroxyphthalimide esters with 1,4-diiodobenzene analogues has been developed. Under mild reaction conditions, a series of structurally interesting 1,4-dialkylbenzene analogues have been accessed with good functional group tolerance, which are versatile precursors for organic synthesis and a kind of important unit for bioactive molecules, polymers, and other materials. The synthetic application of this methodology was demonstrated by the synthesis of 3-6-dialkylcarbazole derivatives.
View Article and Find Full Text PDFJ Am Chem Soc
October 2024
Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.
Organofluorine molecules that contain difluoromethyl groups (CFH) at stereogenic centers have gained importance in pharmaceuticals due to the unique ability of CFH groups to act as lipophilic hydrogen bond donors. Despite their potential, the enantioselective installation of CFH groups into readily available starting materials remains a challenging and underdeveloped area. In this study, we report a nickel-catalyzed decarboxylative difluoromethylation reaction that converts alkyl carboxylic acids into difluoromethylated products with exceptional enantioselectivity.
View Article and Find Full Text PDFScience
September 2024
Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
The myriad nickel-catalyzed cross-coupling reactions rely on the formation of an organonickel intermediate, but limitations in forming monoalkylnickel species have limited options for C(sp) cross-coupling. The formation of monoalkylnickel(II) species from abundant carboxylic acid esters would be valuable, but carboxylic acid derivatives are primarily decarboxylated to form alkyl radicals that lack the correct reactivity. In this work, we disclose a facile oxidative addition and decarbonylation sequence that forms monoalkylnickel(II) intermediates through a nonradical process.
View Article and Find Full Text PDFJ Am Chem Soc
October 2024
National Institute of Biological Sciences, 7 Science Park Road, Zhongguancun Life Science Park, Beijing 102206, China.
Asymmetric decarboxylative cross-couplings of carboxylic acids are powerful methods for synthesizing chiral building blocks essential in medicinal chemistry and material science. Despite their potential, creating versatile chiral alkylboron derivatives through asymmetric decarboxylative C(sp)-C(sp) cross-coupling from readily available primary aliphatic acids and mild organometallic reagents remains challenging. In this study, we present a visible light-induced Ni-catalyzed enantioconvergent C(sp)-C(sp) cross-coupling of unactivated primary aliphatic acid NHPI esters with -borazirconocene alkanes, producing a diverse array of valuable chiral alkylboron building blocks.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Interdisciplinary Nanoscience Center (iNANO), Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark.
Here we present an effective nickel-catalyzed carbonylative cross-coupling for direct access to alkyl aryl ketones from readily accessible redox-activated tetrachlorophthalimide esters and aryl boronic acids. The methodology, which is run employing only 2.5 equivalents of CO and simple Ni(II) salts as the metal source, exhibits a broad substrate scope under mild conditions.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!