Tin Hydride Reductions
Modern Methods for Radical Deoxygenation of Alcohols,
Hartwig, W. Tetrahedron 1983, 39, 2609.
Tributyltin Hydride as Reagent in Organic Synthesis,
Neumann, W. P. Synthesis 1987, 665.
Reductive Cleavage of Aliphatic Nitro Compounds,
Ohno, N.; Kaji, A. Syntheses 1986, 693-704.
Metal-Catalyzed Hydrostannations,
Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257-82.
Tin Hydride Substitutes in Reductive Radical Chain Reactions,
Studer, A.; Amrein, S. Synthesis 2002, 835-49.
Ionic Activation of Tin Hydrides,
Shibata, I.; Baba, A. Curr. Org. Chem. 2002, 6, 665-93.
Tin hydrides have the almost unique ability among metal hydrides to support radical chain reductions of a variety of C-X bonds (X = Cl, Br, I, SePh, SPh, NO2, OC(=S)R). They are thus commonly used for removal of unwanted functional groups.
The radical chains are typically initiated with the radical initiator AIBN.
Free Radical Chain Reductions with Tin Hydrides.
Corey, TL, 1981, 22, 1587.
Tertiary, and sometimes secondary nitro groups are reductively removed with tin hydrides: Ono, TL, 1982, 23, 2957
Use of a vinyl-nitro compound as a Michael acceptor, followed by reductive removal of the nitro group: Prostaglandin E1. Tanaka, T.; Toru, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Kurozumi, S.; Suzuki, M.; Kawagishi T.; Noyori, R. Tetrahedron Lett. 1983, 24, 4103-4104. DOI
Thromboxane A2 Model System: Still TL, 1985, 26, 1955.
Deoxygenation of Secondary Alcohol Thiocarbonates - Barton-McCombie reduction.
Robins, JACS, 1981, 103, 932.
Solanapyrone: Hagiwara, H.; et al. J. Org. Chem. 2002, 67, 5969
Below and example of the use of a carbonyl group to introduce three substituents, followed by reductive removal of the ketone function. Sordaricin: Mander, L. N.; Thomson, R. J. Org. Lett. 2003, 5, 1321. DOI
