Lithium triethylborohydride

Commonly referred to as LiTEBH or Superhydride, it is a powerful reducing agent used in organometallic and organic chemistry.

Instead, LiBHEt3 is reserved for difficult substrates, such as sterically hindered carbonyls, as illustrated by reduction of 2,2,4,4-tetramethyl-3-pentanone.

With unsymmetrical epoxides, the reaction can proceed with high regio- and stereo- selectivity, favoring attack at the least hindered position: Acetals and ketals are not reduced by LiBHEt3.

[5] LiBHEt3 can selectively deprotect tertiary N-acyl groups without affecting secondary amide functionality.

[8] LiBHEt3 reacts exothermically, potentially violently, with water, alcohols, and acids, releasing hydrogen and the pyrophoric triethylborane.

Skeletal formula of lithium triethylborohydride
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid