Simple as ABC: Alkynyl borane cycloadditions can be substrate-directed to assemble aromatic difluoroboranes within an extremely mild and efficient reaction manifold compared to that of traditional methods (see scheme). The aromatic boranes are readily transformed into a range of useful products.
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http://dx.doi.org/10.1002/anie.201200917 | DOI Listing |
Org Biomol Chem
December 2024
Fluoro-Agro chemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
J Org Chem
May 2024
Key Laboratory of Xin'an Medicine, Ministry of Education, Anhui University of Chinese Medicine, Hefei, Anhui 230038, P. R. China.
Herein, a new intramolecular palladium(II)-catalyzed regioselective 6- or 6- annulation through direct C-H activation is presented as a method for the diversity-oriented synthesis of highly substituted quinolinones from pyridones. The reaction occurs under mild conditions and exhibits excellent regioselectivity, good functional group tolerance, and broad applications. This innovative approach has been successfully utilized in the synthesis of Glycopentanolone A and an intermediate of ()-(+)-Tipifarnib.
View Article and Find Full Text PDFOrg Lett
November 2023
Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, PR China.
With triethylamine as a 1,3-diene variant, a simple and practical process for the synthesis of phthalimides has been developed from readily available maleimide. The transformation can be performed in the absence of a metal catalyst with high levels of functional group tolerance. Various phthalimide compounds were constructed in moderate to good yields under mild conditions.
View Article and Find Full Text PDFNat Chem
February 2024
Department of Chemistry, University of Chicago, Chicago, IL, USA.
1,2-Azaborines represent a unique class of benzene isosteres that have attracted interest for developing pharmaceuticals with better potency and bioavailability. However, it remains a long-standing challenge to prepare monocyclic 1,2-azaborines, particularly multi-substituted ones, in an efficient and modular manner. Here we report a straightforward method to directly access diverse multi-substituted 1,2-azaborines from readily available cyclopropyl imines/ketones and dibromoboranes under relatively mild conditions.
View Article and Find Full Text PDFJ Am Chem Soc
July 2023
Department of Materials, ETH Zürich, Zurich 8093, Switzerland.
The bottom-up synthesis of graphene nanoribbons (GNRs) offers a promising approach for designing atomically precise GNRs with tuneable photophysical properties, but controlling their length remains a challenge. Herein, we report an efficient synthetic protocol for producing length-controlled armchair GNRs (AGNRs) through living Suzuki-Miyaura catalyst-transfer polymerization (SCTP) using RuPhos-Pd catalyst and mild graphitization methods. Initially, SCTP of a dialkynylphenylene monomer was optimized by modifying boronates and halide moieties on the monomers, affording poly(2,5-dialkynyl--phenylene) (PDAPP) with controlled molecular weight ( up to 29.
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