Allylic arylation of cinnamyloxyphenylboronic acid pinacol esters 3, which have arylboronic acid moiety and allylic ether moiety, using a hydrazone 1d-Pd(OAc)2 system proceeded and gave the corresponding 1,3-diarylpropene derivatives 4 with a phenolic hydroxyl group via a selective coupling reaction of the π-allyl intermediate to the boron-substituted position of the leaving group.
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http://dx.doi.org/10.1021/jo501235w | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Shanghai Inst Org Chem, State Key Lab Organometallic Chem, 345 Lingling Lu, 200032, Shanghai, CHINA.
Rhodium-catalyzed regio- and enantioselective allylic arylation of racemic alkyl- and aryl- substituted allylic carbonates with arylboronic acids using commercially available BIBOP ligand is reported. This reaction proceeds at room temperature without base or other additive to deliver allylic arylation products in excellent yields, regio- and enantioselectivity (up to 95% yield, >20:1 b/l, >99% ee). Rh/BIBOP is disclosed as an efficient catalytic system for allylic substitution reaction.
View Article and Find Full Text PDFJ Org Chem
December 2024
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
View Article and Find Full Text PDFJ Org Chem
November 2024
Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, 75005 Paris, France.
Despite conceptual breakthroughs in dual photoredox- and nickel-catalyzed arylation of radicals, the approach remains largely limited to localized C-centered radicals. Here, we extend it to allylic radicals, focusing on -allyl heterocycles. Using [Ir(dF(CF)ppy)(dtbbpy)]PF and NiCl(dtbbpy) under visible light, we achieve regioselective γ-amino radical arylation, yielding enamines in good yields.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China.
Chemistry
January 2025
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau, 79104, Germany.
Reliable radical precursors are crucial for photocatalytic processes. In particular, heteroatom-stabilized radicals have attracted considerable research interest in photocatalysis. Among them, α-amino radicals have received the most attention, while the research on α-hydroxy radicals is much less developed.
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