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Herein, we report a copper(I)-catalyzed enantioselective addition of diarylphosphine sulfides to -thiophosphinoyl aldimines. The reaction offers some advantages, such as mild conditions, an easy protocol, and high enantioselectivity. Control experiments indicate that the "soft-soft" interactions between the copper(I) catalyst and the sulfur atoms in both diarylphosphine sulfides and -thiophosphinoyl aldimines facilitate the addition.
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http://dx.doi.org/10.1039/d5ob00682a | DOI Listing |
Org Biomol Chem
June 2025
State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Herein, we report a copper(I)-catalyzed enantioselective addition of diarylphosphine sulfides to -thiophosphinoyl aldimines. The reaction offers some advantages, such as mild conditions, an easy protocol, and high enantioselectivity. Control experiments indicate that the "soft-soft" interactions between the copper(I) catalyst and the sulfur atoms in both diarylphosphine sulfides and -thiophosphinoyl aldimines facilitate the addition.
View Article and Find Full Text PDFJ Org Chem
October 2024
College of Chemistry, International Phosphorus Laboratory, Zhengzhou University, Zhengzhou 450001, China.
New reactions of benzyl phosphine oxide/sulfide with oxalyl chloride are presented. The resulting reactive intermediates, acyl chloride-substituted chlorophosphonium ylides, are capable of undergoing esterification and Friedel-Crafts acylation reactions, ultimately yielding either methyl 2-(2-bromophenyl)-2-(diphenylphosphoryl)acetate or β-carbonyl-diarylphosphine oxide derivatives. Additionally, when an alkynyl group is contained in the acyl chloride-substituted chlorophosphonium ylide, intramolecular cyclization occurs, leading to the formation of a pair of and dichlorophosphonyl benzofulvene isomers.
View Article and Find Full Text PDFJ Am Chem Soc
June 2017
Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
A novel approach to produce chiral diaryl sulfoxides from aryl benzyl sulfoxides and aryl bromides via an enantioselective arylation of aryl sulfenate anions is reported. A (JosiPhos)Pd-based catalyst successfully promotes the asymmetric arylation reaction with good functional group compatibility. A wide range of enantioenriched diaryl, aryl heteroaryl, and even diheteroaryl sulfoxides were generated.
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