Benzylic zinc reagents prepared by direct insertion of zinc to benzylic chlorides in the presence of LiCl undergo smooth cross-coupling reactions with aromatic chlorides, bromides and tosylates using Ni(acac)(2) and PPh(3) as a catalyst system.
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http://dx.doi.org/10.1039/b803072c | DOI Listing |
J Org Chem
January 2025
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
We have studied copper-catalyzed cross-coupling of chiral α-CF-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp)-C(sp) bond with high selectivity.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Lunan Institute of Intelligent Biomedical Engineering, College of Food Science and Pharmaceutical Engineering, Zaozhuang University, Zaozhuang, 277160, P. R. China.
A silver-catalyzed cross coupling of cyclic aldimines and α-imino-oxy acids has been developed. The solvent-dependent reaction could selectively deliver either cyclic imine moiety retained nitriles or ring-opened oxonitriles in moderate yields. The mechanistic studies show that the reaction undergoes a radical pathway.
View Article and Find Full Text PDFJ Mater Chem B
January 2025
Department of Chemistry, Indian Institute of Technology Indore, Indore 453552, India.
Mechanofluorochromic (MFC) materials are emerging as a versatile candidate for optoelectronic and biomedical applications. In the present work, we designed and synthesized four MFC materials, namely BT-PTZ-1, BT-PTZ-2, BT-PTZO-1, and BT-PTZO-2, using Suzuki cross-coupling reaction. These materials possess benzothiazole (BT) as an acceptor moiety and different donors, including phenothiazine (PTZ) and triphenylamine (TPA), with variations in their spacer units.
View Article and Find Full Text PDFNat Commun
January 2025
State Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, PR China.
Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity. This catalytic reaction can not only be applied to aryl chlorides/bromides, which are challenging to access by other means, but also to benzyl chlorides containing silicon groups. Additionally, the absence of a sacrificial anode lays a foundation for scalability.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080, United States.
A general streamlined strategy for the enantioselective total syntheses of the schizozygane family of natural products and related alkaloid vallesamidine is described. Specifically, a catalytic enantioconvergent cross-coupling sets the quaternary stereogenic center in a pluripotent intermediate adorned with an olefin and three orthogonal carboxylate groups, upon which the modularity of the synthesis relies. A late-stage catalytic oxidative lactamization of an alkyne is instrumental in the first-generation synthesis of the schizozygane alkaloids.
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