title: Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using SmI2 and D2O as deuterium source under SET conditions.
abstract: The first general method for the chemoselective synthesis of α,α-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II) with a Lewis base, results in excellent levels of deuterium incorporation across a wide range of substrates, and represents an attractive alternative to processes mediated by pyrophoric alkali metal deuterides.
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Malcolm
authors.initials: M
authors.lastname: Spain
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003903:Deuterium / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D008672:Metals, Alkali / Q000737:chemistry; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D002264:Carboxylic Acids; D007454:Iodides; D008672:Metals, Alkali; D012493:Samarium; D003903:Deuterium; C409809:samarium diiodide