Electrochemical Reduction of Samarium Triiodide into Samarium Diiodide
نویسندگان
چکیده
منابع مشابه
New samarium diiodide-induced cyclizations*
Samarium diiodide (SmI2) smoothly promotes the cyclizations of suitably substituted carbonyl compounds with styrene subunits leading to benzannulated cyclooctenes. The intramolecular samarium ketyl addition to arene or hetarene moieties enables a new, efficient, and highly stereoselective entry to dearomatized products such as hexahydronaphthalenes, steroid-like tetraor pentacyclic compounds, o...
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Mechanistic studies show the importance of iodide displacement by additives that accelerate reactions of samarium diiodide. The key feature important for acceleration of reaction rate is the use of proton donors and other additives that have a high enough affinity for Sm(II) to displace iodide yet do not saturate the coordination sphere inhibiting substrate reduction.
متن کاملHighly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations
A series of γ-oxo esters suitably substituted with various styrene subunits was subjected to samarium diiodide-induced 8-endo-trig cyclizations. Efficacy, regioselectivity and stereoselectivity of these reactions via samarium ketyls strongly depend on the substitution pattern of the attacked alkene moiety. The stereoselectivity of the protonation of the intermediate samariumorganyl is also infl...
متن کاملA novel reductive cyclization of arylmethylidenemalononitrile promoted by samarium diiodide
Carbon]carbon bond formation is the essence of organic synthesis and the reductive dimerization of carbonyl derivatives is a most valuable method for establishing carbon]carbon bonds. Since the time Kagan demonstrated a simple preparation of samarium diiodide from samarium metal and 1,2-diiodoethane, SmI2 has been developed as a mild, neutral and versatile single electron transfer reductant. It...
متن کاملReduction of acetals with samarium diiodide in acetonitrile in the presence of Lewis acids.
Transformation of acetals into ethers by partial reduction using a samarium diiodide-Lewis acids-acetonitrile system is described. The reaction with aromatic acetals occurred in good yields in the presence of aluminum chloride (2 eq) whereas the corresponding aliphatic, vinylic, and alkynyl derivatives did not afford ethers under the same conditions. Beta-elimination to give an enol ether becom...
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ژورنال
عنوان ژورنال: Chemistry Letters
سال: 2020
ISSN: 0366-7022,1348-0715
DOI: 10.1246/cl.200429