Literature DB >> 21879049

Selective reductive transformations using samarium diiodide-water.

Michal Szostak1, Malcolm Spain, Dixit Parmar, David J Procter.   

Abstract

Samarium diiodide (SmI(2)) is one of the most important reductive electron transfer reagents available in the laboratory. Key to the popularity of SmI(2) is the ability of additives and co-solvents to tune the properties of the reagent. Over the last decade water has emerged as a particularly valuable additive, opening up new chemical space and leading to the discovery of unprecedented selectivity and new reactions promoted by SmI(2). In this Feature Article we review recent progress in the application of SmI(2)-H(2)O systems, with an emphasis on mechanistic considerations and the development of new transformations. This journal is © The Royal Society of Chemistry 2012

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Year:  2011        PMID: 21879049     DOI: 10.1039/c1cc14252f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  10 in total

1.  SmI2(H2O)n Reduction of Electron Rich Enamines by Proton-Coupled Electron Transfer.

Authors:  Scott S Kolmar; James M Mayer
Journal:  J Am Chem Soc       Date:  2017-07-31       Impact factor: 15.419

2.  Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Nat Protoc       Date:  2012-04-26       Impact factor: 13.491

3.  On the role of pre- and post-electron-transfer steps in the SmI2 /amine/H(2)O-mediated reduction of esters: new mechanistic insights and kinetic studies.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Chemistry       Date:  2014-03-11       Impact factor: 5.236

4.  Selective reduction of barbituric acids using SmI2/H2O: synthesis, reactivity, and structural analysis of tetrahedral adducts.

Authors:  Michal Szostak; Brice Sautier; Malcolm Spain; Maike Behlendorf; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-09       Impact factor: 15.336

5.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

6.  Selective Synthesis of Cyclooctanoids by Radical Cyclization of Seven-Membered Lactones: Neutron Diffraction Study of the Stereoselective Deuteration of a Chiral Organosamarium Intermediate.

Authors:  Xavier Just-Baringo; Jemma Clark; Matthias J Gutmann; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-07       Impact factor: 15.336

7.  Development of an additive-controlled, SmI2-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination.

Authors:  Brice Sautier; Karl D Collins; David J Procter
Journal:  Beilstein J Org Chem       Date:  2013-07-18       Impact factor: 2.883

8.  Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions.

Authors:  Michal Szostak; Malcolm Spain; Andrew J Eberhart; David J Procter
Journal:  J Am Chem Soc       Date:  2014-01-31       Impact factor: 15.419

9.  Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors:  Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal:  Chemistry       Date:  2015-11-26       Impact factor: 5.236

Review 10.  Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide.

Authors:  Shicheng Shi; Michal Szostak
Journal:  Molecules       Date:  2017-11-21       Impact factor: 4.411

  10 in total

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