An environmentally benign and highly efficient procedure has been developed for the direct one-pot synthesis of beta-hydroxysulfides in good yields under neutral conditions from alkenes and thiophenols in the presence of aerial oxygen using beta-cyclodextrin in water. This protocol tolerates a wide variety of functional groups or substrates and does not require the use of either acid or base catalysts. beta-Cyclodextrin can be recovered and reused for a number of runs without any loss of activity.
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http://dx.doi.org/10.1021/jo060805a | DOI Listing |
J Org Chem
July 2024
Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Hunan Province Key Laboratory of Green Organic Synthesis and Application, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
A copper-catalyzed three-component coupling reaction of styrene oxide, aryl iodide, and carbon disulfide for the construction of β-hydroxysulfides has been developed. In this process, readily available CS was used as the sulfur source to construct C-S bonds for the synthesis of phenyl-β-hydroxysulfides and (benzo[]thiazol)-β-hydroxysulfides. This process features mild reaction conditions, simple operation, and wide substrate scope (>50 examples).
View Article and Find Full Text PDFChem Asian J
January 2024
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
Transition-mental-free multi-component hydroxysulfenylation of styrenes with NH SCN and water to from β-hydroxysulfides is established. The reaction mechanism proceeded via a domino reaction after a radical addition to 2-phenylimidazo[1,2-a]pyridines. This approach features a wide substrate scope and functional group compatibility, providing 34 compounds in acceptable yields.
View Article and Find Full Text PDFACS Omega
May 2023
Organic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India.
The visible-light-promoted catalyst-free condition has been demonstrated for self- and cross-coupling reactions of thiols in an ambient atmosphere. Further, synthesis of β-hydroxysulfides is accomplished under very mild conditions involving the formation of an electron donor-acceptor (EDA) complex between a disulfide and an alkene. However, the direct reaction of thiol with alkene the formation of a thiol-oxygen co-oxidation (TOCO) complex failed to produce the desired compounds in high yields.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2022
School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, London, SE1 9NH, UK.
Chiral β-hydroxysulfides are an important class of organic compounds which find broad application in organic and pharmaceutical chemistry. Herein we describe the development of novel biocatalytic and chemoenzymatic methods for the enantioselective synthesis of β-hydroxysulfides by exploiting ketoreductase (KRED) enzymes. Four KREDs were discovered from a pool of 384 enzymes identified and isolated through a metagenomic approach.
View Article and Find Full Text PDFJ Org Chem
September 2021
Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, and Chemistry and Chemical Engineering Laboratory of Guangdong Province, Shantou University, Shantou, Guangdong 515063, P. R. China.
A light-promoted and tertiary-amine-assisted strategy for efficient hydroxysulfenylation of both electron-rich and electron-deficient alkenes with thiophenols to selectively and directly access β-hydroxysulfides in one pot is described herein. In contrast to the previously reported thiol-oxygen co-oxidation reactions, this simple and sustainable approach features mild reaction conditions, high efficiency, and excellent functional group tolerance.
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