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Cu-Promoted Divergent Phosphination of Alkynylsulfonium Salts with Diarylphosphines.
Org Lett
September 2024
College of Materials, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China.
An efficient copper-promoted divergent phosphination of alkynylsulfonium salts with secondary diarylphosphines that tolerates a wide range of functional groups under mild conditions is reported. The use of excess alkynyl dibenzothiophenium salts (/ > 1, mole ratio) enables the phosphination to deliver alkynyl monophosphine products via a C(sp)-P cross-coupling in good to high yields, while the use of excess secondary diarylphosphines (/ < 0.5, mole ratio) leads to a type of -ethenyl bisphosphine products via sequential stereoselective double phosphination.
View Article and Find Full Text PDFStereoselective Fluorosulfonylation of Vinylboronic Acids for ()-Vinyl Sulfonyl Fluorides with Copper Participation.
Org Lett
March 2024
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, P. R. China.
A practical synthetic method for the synthesis of vinyl sulfonyl fluorides through copper-promoted direct fluorosulfonylation has been developed. The reaction of the vinylboronic acids with DABSO and then NFSI is performed under mild reaction conditions. This transformation efficiently affords aryl or alkyl vinyl sulfonyl fluorides with good reaction yields, exclusive -configuration, broad substrate scope, excellent compatibility, and operational simplicity.
View Article and Find Full Text PDFCopper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides.
Beilstein J Org Chem
January 2024
Jiangsu Provincial Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, 223300, Jiangsu, China.
An efficient and practical method for the synthesis of C5-brominated 8-aminoquinoline amides via a copper-promoted selective bromination of 8-aminoquinoline amides with alkyl bromides was developed. The reaction proceeds smoothly in dimethyl sulfoxide (DMSO) under air, employing activated and unactivated alkyl bromides as the halogenation reagents without additional external oxidants. This method features outstanding site selectivity, broad substrate scope, and excellent yields.
View Article and Find Full Text PDFSynthesis of 2-amino-9-chromeno[2,3-]thiazol-9-ones with anti-inflammatory activity cascade reactions of 2-amino-3 iodochromones with amines and carbon disulfide.
RSC Adv
January 2024
State Key Laboratory of Drug Research, Shanghai Institute of Materia, Medica, Chinese Academy of Sciences 555 Zuchongzhi Road Shanghai 201203 China
A simple and efficient synthetic approach to 2-amino-9-chromeno[2,3-]thiazol-9-ones copper-promoted cascade reactions was developed. The reaction employed easily available 2-amino-3-iodochromones and amines as substrates and the targeting tricyclic compounds could be obtained with moderate to good yields. Even more important, several synthesized compounds exhibited potent anti-inflammatory activities, which suggested that this protocol may provide valuable hits for drug development in the future.
View Article and Find Full Text PDFSynthesis and Anti-Inflammatory Activity of (2)-Arylindazol-3(2)-One Derivatives: Copper-Promoted Direct -Arylation via Chan-Evans-Lam Coupling.
Molecules
September 2023
Department of Applied Chemistry, Global Center for Pharmaceutical Ingredient Materials, Kyung Hee University, Yongin-si 17104, Gyeonggi, Republic of Korea.
Inflammatory-related diseases are becoming increasingly prevalent, leading to a growing focus on the development of anti-inflammatory agents, with a particular emphasis on creating novel structural compounds. In this study, we present a highly efficient synthetic method for direct -arylation to produce a variety of (2)-arylindazol-3(2)-ones , which exhibit anti-inflammatory activity. The Chan-Evans-Lam (CEL) coupling of (1)-benzyl-indazol-3-(2)-ones with arylboronic acids in the presence of a copper complex provided the corresponding (2)-arylindazol-3(2)-ones in good-to-excellent yields, as identified with NMR, MS, and X-ray crystallography techniques.
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