A Stille cross-coupling reaction was developed that delivers for the first time trifluoromethyl-substituted homoallyl compounds from α-(trifluoromethyl)benzyl chlorides and allylstannanes. This reaction proceeds even with low catalyst loadings (1 mol%) via a rare CF3-Pd-π-benzyl intermediate.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8cc03541e | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Stereocontrolled Synthesis of the Portimine Skeleton via Organocatalyst-Mediated Asymmetric Stannylation and Stereoretentive C()-C() Stille Coupling.
Org Lett
January 2025
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, 980-8577 Aoba-ku, Sendai, Japan.
Our efforts toward the synthesis of the marine natural product portimine are described. The key to the synthesis of the skeleton is a stereoretentive copper-catalyzed C()-C() Stille-type cross-coupling that enables the convergent assembly of functionalized fragments. The core skeleton of portimine was constructed via ring-closing metathesis and transannular acetal formation.
View Article and Find Full Text PDFIntroduction of Molecular Complexity via the Cross-Coupling of Lithium 1,4-Dioxene with Aryl Bromides.
Chemistry
November 2024
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
The synthetic potential of substituted 1,4-dioxenes is well recognised, although the chemistry of 2-aryl-1,4-dioxenes is relatively unexplored. Their transition metal-catalysed synthesis has been limited to Stille-type cross-coupling chemistry, typically showing long reaction times, or proceeding at high reaction temperatures. Here we present a facile and general methodology for the cross-coupling of aryl bromides with lithium 1,4-dioxene, affording a range of 2-aryl-1,4-dioxenes in generally good yields.
View Article and Find Full Text PDFThe Preparation of Dithieno[3,2-:4,5-']germole, and Its Application as a Donor Unit in Conjugated D-A Compounds.
Molecules
July 2024
Smart Innovation Program, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan.
Group 14 metalloles have attracted much attention as core structures of conjugated functional materials. In this work, we prepared dithieno[3,2-:4,5-']germole as a new unsymmetrically condensed dithienogermole and benzo[4,5]thieno[2,3-c]germole as the benzene-condensed analog. The electronic states and properties of these unsymmetrically condensed germoles are discussed on the basis of the results of optical and electrochemical measurements with the help of quantum chemistry calculations on the simplified model compounds.
View Article and Find Full Text PDFC-S-Selective Stille-Coupling Enables Stereodefined Alkene Synthesis.
Angew Chem Int Ed Engl
October 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, MOE Key Laboratory of Geriatric Diseases and Immunology, Suzhou Key Laboratory of Pathogen Bioscience and Anti-infective Medicine, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 215123, Suzhou, China.
A palladium-catalyzed highly C-S-selective Stille cross-coupling between aryl thianthrenium salts and tri- or tetrasubstituted alkenyl stannanes is described. Herein, critical challenges including site- and chemoselectivity control are well addressed through C-H thianthrenation and C-S alkenylation, thereby providing an expedient access to stereodefined tri- and tetrasubstituted alkenes in a stereoretentive fashion. Indeed, the palladium-catalyzed Stille-alkenylation of poly(pseudo)halogenated arenes displays privileged capability to differentiate C-S over C-I, C-Br, C-Cl bonds, as well as oxygen-based triflates (C-OTf), tosylates (C-OTs), carbamates and sulfamates under mild reaction conditions.
View Article and Find Full Text PDFTotal Synthesis and Bioactivity Profile of (+)-Ieodomycins A and B and their Stereoisomers.
ACS Omega
June 2024
Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology (KIOST), Busan 49111, Republic of Korea.
Herein, we report the first- and second-generation syntheses of (+)-ieodomycins A and B and their stereoisomers via the late-stage elaboration of their conjugated -diene side chains. Key steps for successful synthesis included Keck asymmetric allylation to introduce a hydroxyl group at the C5 position, consecutive Wipf's carboalumination modification, iodination, Sharpless asymmetric dihydroxylation, one-carbon homologation via cyanation, Mukaiyama lactonization, and Stille cross-coupling to form the conjugated -diene moiety. Further, the preliminary bioactivity profile against various disease-related molecular targets and cell lines was investigated.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!