Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Brønsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.
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http://dx.doi.org/10.1021/acs.joc.1c01277 | DOI Listing |
Chem Asian J
January 2025
Nanjing University, School of Chemistry and Chemial Engineering, 163 Xianlin Avenue, 210023, Nanjing, CHINA.
Axial chiral biaryl skeletons are widely found in biologically active molecules, catalysts and chiral functional materials. However, highly catalytic stereoselective synthesis of tetra-ortho-substituted biaryls remains a challenging task. In this paper, we describe an efficient approach for construction of axially tetra-ortho-substituted biaryls via Suzuki-Miyaura coupling in the presence of a chiral monophosphate ligand developed by ourselves.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States.
We present the serendipitous discovery of an unusual dimer formed from anthracene-derived polyarenes. Unlike the typical oxidative coupling of substituted aromatic scaffolds, the reaction yielded a dearomatized enone dimer as the sole product. This dearomatized motif, notably, does not undergo the commonly observed rearomatization, and no biaryl products were detected.
View Article and Find Full Text PDFLangmuir
January 2025
Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran.
Org Lett
January 2025
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization of prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables the efficient synthesis of a wide range of densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities.
View Article and Find Full Text PDFMolecules
November 2024
Catalyse Organométallique, Synthèse Organique et Santé (COSyS), Institut de Chimie (UMR-CNRS 7177), Université de Strasbourg, 67000 Strasbourg, France.
Due to the importance of biaryls as natural products, drugs, agrochemicals, dyes, or organic electronic materials, a green alternative biaryl synthesis has been developed based on easy-to-prepare and cheap copper(I)-exchanged zeolite catalysts. Cu-USY proved to efficiently catalyze the direct homocoupling of either phenols or aryl boronic acids under simple and practical conditions. The Cu-USY-catalyzed oxidative homocoupling of phenols could conveniently be performed under air either in warm methanol or water with good to high yields.
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