Samarium(ii) iodide (smi2) is a mild one-electron reducing agent used for various reductive reactions of carbonyl compounds, organic halides, and electron kilo-scale synthesis of chemotherapy drug halaven: the highly selective reduction was achieved by careful optimization of reaction conditions. Samarium(ii) iodide (smi 2, also known as kagan's reagent) is a green solid composed of samarium and iodine, with a melting point of 520 °c where the samarium atom has a coordination number of seven in a capped octahedral configuration it can be formed by high temperature decomposition of samarium( iii) iodide. Sml 2 -mediated reductive couplings of acrylates/crotonates for diverted total synthesis of designed macrolactones, (-)-palmyrolide a and laingolide a have provided many exciting opportunities in the metal-catalyzed reactions and reductive chemistry in organic chemistry area, with samarium diiodide (smi2) being the. Samarium(ii) iodide (smi2) is one of the most important reducing agents in organic synthesis synthetic factors such as water, oxygen, and peroxide content in thf have little influence on the synthesis of smi2 beyond samarium diiodide: vistas in reductive chemistry mediated by lanthanides(ii.
Scope of a novel three-component synthesis of highly functionalized pyridines j dash, t lechel, hu reissig organic letters 9 (26), 5541-5544, 2007 72, 2007 novel stereoselective syntheses of highly functionalized benzannulated pyrrolizidines and indolizidines by samarium diiodide induced cyclizations of indole. Introduced by henri kagan more than three decades ago, samarium diiodide ( smi2) has found increasing application in chemical synthesis of the power of this reagent in the construction of complex molecules and inspirational for the design of synthetic strategies toward such targets, both natural and. The use of samarium diiodide in organic and polymer synthesis n e brandukova , ya s vygodskii, s v vinogradova contents i introduction ii the synthesis and properties of divalent lanthanide salts iii reactions involving samarium diiodide 345 345 346 abstract the methods of synthesis and properties of samarium. Keywords: chemistry, issue 72, organic chemistry, chemical engineering, biochemistry, samarium diiodide, sml2, samarium-barbier reaction, hmpa, hexamethylphosphoramide, ni(ii), nickel(ii) acetylacetonate, nickel, samarium, iodine, additives, synthesis, catalyst, reaction, synthetic organic chemistry.
(5)for recent reviews on reductions with samarium diiodide, including examples of n-o reductive cleavage, see: (a) imamoto, t lanthanides in organic synthesis academic press: london, 1994 p 38-39 (b) molander, g a org react 1994, 46, 211 (6) (a) chiara, j l marco-contelles, j khiar, n gallego, p destabel. Scope of a novel three-component synthesis of highly functionalized pyridines j dash, t lechel, hu reissig organic letters 9 (26), 5541-5544, 2007 73, 2007 novel stereoselective syntheses of highly functionalized benzannulated pyrrolizidines and indolizidines by samarium diiodide induced cyclizations of indole.
Aromatic carboxylic acids, esters, amides, nitriles, chlorides, ketones and nitro compounds were rapidly reduced by the samarium diiodide–h2o system to the corresponding products at room temperature in good a facile synthesis of 2,3- dihydroxyketones from 1,2-diketones and aldehydes using samarium diiodide. Keywords: samarium iodide nitrogen heterocycles nitrogen radicals reductive coupling smi2 radical cyclizations samarium diiodide umpolung cyclizations aminoketyl radicals 1 introduction since its introduction to organic synthesis by kagan in 1980, samarium diiodide (smi2, kagan's reagent) has. An effective single-electron reducing agent for the promotion of ketone-olefin and pinacol coupling reactions under mild conditions often both intramolecular and intermolecular couplings proceed in a highly stereoselective fashion starting material for the synthesis of new heteroleptic samarium aryloxide/ cyclopentadienide.
An intermolecular pinacol coupling of aromatic or aliphatic carbonyl compounds catalyzed by a complex of samarium diiodide (smi2) with tetraglyme in the a highly efficient, mild and practical approach for the synthesis of optically pure β- amino alcohols by the smi2-induced reductive cross-coupling of various chiral.
Intramolecular reductive coupling of carbonyl-tethered oxime ethers promoted by samarium diiodide: a powerful method for the stereoselective synthesis of aminocy jl chiara, j marco-contelles, n khiar, p gallego, c destabel, m bernabe the journal of organic chemistry 60 (19), 6010-6011, 1995 74, 1995 exploring. First used in organic chemistry by kagan and coworkers in 1977, samarium diiodide (smi2) has since been employed in the development of a wide variety of reactions and featured in hundreds of syntheses the large reduction potential of smi2 (up to −205 v in the presence of hmpa) allows access to a rich array of.
Samarium metal original commentary gary a molander & christina r harris university of colorado, boulder, co, usa reduction of organic halides and related substrates alkyl halides smi2-promoted barbier reaction towards the synthesis of hin- diodide to generate dienolates which are kinetically trapped at. In 1979, kagan observed the reduction of a variety of organic functional groups by samarium iodide under mild reaction conditions since that time, samarium iodide has been employed in a variety of contexts in organic synthesis for both functional group manipulation and carbon-carbon bond formation samarium iodide is. Get expert answers to your questions in organic synthesis, synthesis of organic molecules, samarium and thin layer chromatography and more on researchgate, the professional network for scientists. Organic synthesis4 of these lanthanides, samarium diiodide has been the most attractive reagent the efforts in this area substantiate the unique role samarium diiodide can play in promoting reactions that are very difficult to accomplish by other available reagents5 the success of the samarium diiodide reaction, however.