A selective reducing reagent ideal for reductive aminations that can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound.1 Used in tin-free Giese reaction of alkyl iodides with electron-deficient alkenes,2 preparation of primary amines by reductive amination of aldehydes and hemiacetals with no or minimal formation of the usual secondary and tertiary amine byproduct,3 intermolecular hydroamination of terminal alkynes,4 conversion of some heterocyclic aldehydes to esters,5 intramolecular reductive cyclization of diketoximes to afford N-hydroxy heterocycles,6 and reductive N-alkylation with acetone and levulinic acid.7 Also applied in hydrogenolysis reactions, such as the opening of acetals.8
Reference
1. Tetrahedron Lett. 2009, 50, 6658.
2. Org. Lett., 2008, 10, 1005.
3. J. Org. Chem., 2010, 75, 5470.
4. Org. Lett., 2003, 5, 4767.
5. Synth. Comm. 2011, 41, 2505.
6. Org. Biomol. Chem. 2011, 9, 4642.
7. Int. J. Biol. Macromol. 2010, 47, 184.
8. Tetrahedron 1995, 51, 3339.