Lithium triethylborohydride, LiTEBH, Superhydride
LiBHEt3 is a very strong reducing agent, that is even more efficient than lithium aluminum hydride. LiTEBH for examples enables a fast reduction of carbonyl compounds, esters, acid chlorides, acid anhydrides and tertiary amides to alcohols and disulfides to thiols.
Recent Literature
Primary alcohols can be deoxygenated cleanly and in good yields by reduction of
derived diphenyl phosphate esters with lithium triethylborohydride in THF at
room temperature. Primary alcohols can selectively be reduced in the presence of
secondary alcohols. An additional one pot two-step process makes the process
simple and convenient.
S. Chowdhury, R. F. Standaert, J. Org. Chem.,
2016, 81, 9957-9963.
Reduction of (RS)-N-tert-butanesulfinyl α-halo
imines with NaBH4 in THF, in the presence of 10 equiv of MeOH, and
subsequent cyclization with KOH afforded the corresponding (RS,S)-N-(tert-butylsulfinyl)aziridines
in quantitative yields. On the contrary, its epimer, (RS,R)-N-(tert-butylsulfinyl)aziridine
was synthesized in good yields and diastereoselectivity by switchover of the
reducing agent from NaBH4 to LiBHEt3.
B. Denolf, E. Leemans, N. De Kimpe, J. Org. Chem., 2007,
72, 3211-3217.