Synthesis of Alkenyl Sulfides Through the Iron-Catalyzed Cross-Coupling Reaction of Vinyl Halides with Thiols.
Summary of "Synthesis of Alkenyl Sulfides Through the Iron-Catalyzed Cross-Coupling Reaction of Vinyl Halides with Thiols."
We report here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works devoted on the coupling of thiols with alkyl vinyl iodides. Interestingly, the known S-vinylation of vinyl bromides and chlorides are limited to 1-(2-bromovinyl)benzene and 1-(2-chlorovinyl)benzene. Investigation on the coupling reaction of challenging alkyl vinyl bromides and chlorides with thiols is rare. Since the coupling of 1-(2-bromovinyl)benzene and 1-(2-chlorovinyl)benzene with thiols can be performed in the absence of any catalyst, here we focus on the coupling of thiols with alkyl vinyl halides. It is important to note that this system is not only reactive for alkyl vinyl iodides but also for the challenging alkyl vinyl bromide and chloride. Interestingly, the regioisomers are formed in most cases when alkyl vinyl chloride is used as the coupling partner; the reason is not clear at the moment.
Affiliation
Journal Details
This article was published in the following journal.
Name: The Journal of organic chemistry
ISSN: 1520-6904
Pages:
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22708836
- DOI: http://dx.doi.org/10.1021/jo3008397
Medical and Biotech [MESH] Definitions
Iron, Dietary
Iron or iron compounds used in foods or as food. Dietary iron is important in oxygen transport and the synthesis of the iron-porphyrin proteins hemoglobin, myoglobin, cytochromes, and cytochrome oxidase. Insufficient amounts of dietary iron can lead to iron-deficiency anemia.
Oxidative Coupling
The reaction of two molecular entities via oxidation usually catalyzed by a transition metal compound and involving dioxygen as the oxidant.
Heavy Chain Disease
A disorder of immunoglobulin synthesis in which large quantities of abnormal heavy chains are excreted in the urine. The amino acid sequences of the N-(amino-) terminal regions of these chains are normal, but they have a deletion extending from part of the variable domain through the first domain of the constant region, so that they cannot form cross-links to the light chains. The defect arises through faulty coupling of the variable (V) and constant (C) region genes.
Iron Regulatory Protein 2
A multifunctional iron-sulfur protein that is both an iron regulatory protein and cytoplasmic form of aconitate hydratase. It binds to iron regulatory elements found on mRNAs involved in iron metabolism and regulates their translation. Its rate of degradation is increased in the presence of IRON.
Iron Regulatory Protein 1
A multifunctional iron-sulfur protein that is both an iron regulatory protein and cytoplasmic form of aconitate hydratase. It binds to iron regulatory elements found on mRNAs involved in iron metabolism and regulates their translation. Its RNA binding ability and its aconitate hydrolase activity are dependent upon availability of IRON.
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