A site-selective catalytic incorporation of multiple CO molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.
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http://dx.doi.org/10.1021/jacs.7b13220 | DOI Listing |
Acc Chem Res
April 2024
Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai 200444, China.
ConspectusTransition metal-catalyzed reductive cross-coupling of two carbon electrophiles, also known as cross-electrophile coupling (XEC), has transformed the landscape of C-C coupling chemistry. Nickel catalysts, in particular, have demonstrated exceptional performance in facilitating XEC reactions, allowing for diverse elegant transformations by employing various electrophiles to forge C-C bonds. Nevertheless, several crucial challenges remain to be addressed.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2023
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, Guangdong, P. R. China.
Functionalizing specific positions on a saturated alkyl molecule is a key challenge in synthetic chemistry. Herein, a ligand-controlled regiodivergent alkylations of alkyl bromides at different positions by Ni-catalyzed alkyl-alkyl cross-electrophile coupling with the second alkyl bromides has been developed. The reaction undergoes site-selective isomerization on one alkyl bromides in a controlled manner, providing switchable access to diverse alkylated structures at different sites of alkyl bromides.
View Article and Find Full Text PDFChem Sci
January 2022
Department of Chemistry, Iowa State University Ames IA 50011 USA
Advances in site-selective functionalization reactions have enabled single atom changes on the periphery of a complex molecule, but reaction manifolds that enable such changes on the core framework of the molecule remain sparse. Here, we disclose a strategy for carbon-to-oxygen substitution in cyclic diarylmethanes and diarylketones to yield cyclic diarylethers. Oxygen atom insertion is accomplished by methylene and Baeyer-Villiger oxidations.
View Article and Find Full Text PDFChemistry
August 2021
Departamento de Química Inorgánica, Universidad de Sevilla, Aptdo 1203, 41071, Sevilla, Spain.
Ni-catalyzed C-S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C-O electrophiles in this context is almost uncharted.
View Article and Find Full Text PDFJ Am Chem Soc
October 2018
Institute of Chemical Research of Catalonia (ICIQ) , The Barcelona Institute of Science and Technology, Av. Països Catalans 16 , 43007 Tarragona , Spain.
A mild, chemo- and site-selective catalytic protocol that allows for incorporating an alkylboron fragment into unactivated olefins is described. The use of internal olefins enables C-C bond-formation at remote sp C-H sites, constituting a complementary and conceptually different approach to existing borylation techniques that are currently available at sp centers.
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