An atom-economic protocol for the efficient and highly chemo- and stereoselective -hydroarylation of ynamides with hydroxyarenes catalyzed by B(CF) has been developed. Use of readily available starting materials, low catalyst loading, mild reaction conditions, a broad substrate scope, ease of scale-up, and versatile functionalizations of the enamide products make this approach very practical and attractive.
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http://dx.doi.org/10.1021/acs.orglett.2c00574 | DOI Listing |
Acc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
View Article and Find Full Text PDFOrg Lett
September 2024
School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China.
Pyrrolocarbazole skeletons are well known to possess a variety of biological activities that might be therapeutically useful in the treatment of cancers. Herein, an acid-catalyzed stereoselective hydroarylation/Diels-Alder cycloaddition/aromatization of ynamide-indoles is described. We newly designed and synthesized a variety of piperazine-fused pyrrolocarbazole derivatives that could be further applied to the synthesis of potent Wee1 inhibitors.
View Article and Find Full Text PDFJ Org Chem
January 2024
School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
Presented herein is a copper-catalyzed -hydroarylation of ynamides. The reaction showcases the assembly of boronic acids across the carbon-carbon triple bond of ynamides. The reaction proceeds under mild conditions offering a complementary approach for the versatile synthesis of multifunctional ()-α,β-disubstituted enamides.
View Article and Find Full Text PDFOrg Lett
April 2022
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.
J Org Chem
March 2022
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Regioselective C-H alkenylation of -dialkylanilines with ynamides was developed using AgNTf as a catalyst. This approach represents a facile hydroarylation of ynamides, allowing for the introduction of an alkenyl group exclusively at the position of aniline derivatives. As a result, a series of 4-alkenyl -dialkylanilines were synthesized with excellent regioselectivities.
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