title: A practical in situ generation of the Schwartz reagent. Reduction of tertiary amides to aldehydes and hydrozirconation.
abstract: A new, highly efficient in situ protocol (Cp2ZrCl2/LiAlH(OBu-t)3) is described for the generation of the Schwartz reagent which provides a convenient method for the amide to aldehyde reduction and the regioselective hydrozirconation-iodination of alkynes and alkenes. Highlighted are chemoselective reductions of benzamides derived by directed ortho metalation (DoM) chemistry, allowing the synthesis of valuable 1,2,3-substituted benzaldehydes. The single-step, three-component process proceeds in a very short reaction time, shows excellent functional group compatibility, and uses inexpensive and long-storage stable reducing reagents.
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
authors.forename: Yigang
authors.initials: Y
authors.lastname: Zhao
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus