LAH, Lithium aluminum hydride, Lithium tetrahydridoaluminate
LiAlH4 is a very common, strong reducing agent, which reduces a vast number of different functional groups.
Recent Literature
The preparation of alkenyl halides of any length from inexpensive starting
reagents is reported. Standard organic transformations were used to prepare
straight-chain α-olefin halides in excellent overall yields with no
detectable olefin isomerization and full recovery of any unreacted starting
material.
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.
Phenol carbamates undergo an anionic ortho-Fries rearrangement to
their corresponding amides in the presence of LDA. Sterically hindered
substrates can be converted with s-BuLi/TMEDA at -90°C. The amides can be efficiently reduced with lithium aluminum hydride
to the corresponding Mannich bases.
N. Assimomytis, Y. Sariyannis, G. Stavropoulos, P. G. Tsoungas, G. Varvounis, P.
Cordopatis, Synlett, 2009,
2777-2782.
Trifluoromethyl arenes were reduced with lithium aluminum hydride to give
toluene derivatives in good yields in the presence of 5 mol % of niobium(V)
chloride. Stepwise, partial reduction of a bis(trifluoromethyl) arene was
also demonstrated.
K. Fuchibe, Y. Ohshima, K. Mitomi, T. Akiyama, Org. Lett., 2007,
9, 1497-1499.
Treatment of substituted arylbromides with tert-butyllithium in diethyl
ether at -78˚C, followed by the addition to dichlorodiethoxysilane, leads to the
quantitative formation of diaryldiethoxysilanes. Diaryldiethoxysilanes can be
reduced to the corresponding diarylsilanes by stirring with lithium aluminum
hydride in diethyl ether. This method avoids the handling of gaseous and
explosive dichlorosilane.
P. Gigier, W. A. Herrmann, F. E. Kühn, Synthesis, 2010,
1431-1432.
