Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
作者:Hyowon Seo、Timothy F. Jamison
DOI:10.1021/acs.orglett.9b04235
日期:2019.12.20
radical from unactivated aliphatic carbonyl compounds is an important strategy in organic synthesis. Herein, catalytic generation and use of a ketyl radical for the reductive coupling of aliphatic carbonyl compounds and styrenes by organic photoredoxcatalysis is described. The method is applicable to both aliphatic ketones and aldehydes to afford the corresponding tertiary and secondary alcohols in continuous
Tripyrrolidinophosphoric Acid Triamide as an Activator in Samarium Diiodide Reductions
作者:Chriss E. McDonald、Jeremy D. Ramsey、David G. Sampsell、Julie A. Butler、Michael R. Cecchini
DOI:10.1021/ol102040s
日期:2010.11.19
The electrochemical and spectrophotometric characterization of the complex formed from samariumdiiodide and 4 equiv of tripyrrolidinophosphoric acid triamide (TPPA) is presented. Kinetic studies indicate that the SmI2/TPPA complex possesses reactivity greater than the complex formed between samariumdiiodide and 4 equiv of HMPA. Examples of the use of SmI2/TPPA in synthesis are presented.
Characterization of the complex formed between samarium diiodide and the dehydro dimer of HMPA (diHMPA)
作者:Chriss E. McDonald、Jeremy D. Ramsey、James A. Grant、Kelly A. Howerter
DOI:10.1016/j.tetlet.2009.06.139
日期:2009.9
A new ligand that facilitates samarium diiodide-mediated reductions has been developed. Addition of a solution of samariumdiiodide to the dehydro dimer of hexamethylphosphoramide results in a purple complex which is an excellent reductant for a variety of organic functionalities. The complex was characterized by the kinetics of reduction of 1-bromodecane, visible spectroscopy, and cyclic voltammetry
Under sonochemical conditions, various alkyl halides were converted into the corresponding alcohols in high yields through an aerobicradical reaction promoted by trialkyltin halide/NaBH3CN catalytic system.
An efficient intermolecular carbon-carbon bond formation via SmI2-promoted anion radical alkylation
作者:Osamu Ujikawa、Junji Inanaga、Masaru Yamaguchi
DOI:10.1016/s0040-4039(00)99138-x
日期:1989.1
Anion radicals generated from the corresponding ketones with the efficient one electron transfer system, SmI2-THF-HMPA, attacked a variety of activated olefins at room temperature affording the corresponding addition products in good to excellent yields, some of which are hardly accessible by the conventional nucleophilic alkylation of ketones.