A Quick Guide to

REDUCTIONS IN ORGANIC CHEMISTRY

• LiAlH4 • LiAlH4
• LiBH4 • AlH3
• BH3·L

• i-Bu2AlH • LiAlH4
H2, Pd
i-Bu2AlH • Li(EtO)3AlH • Tf2O,
ROSENMUND
Hantzsch esters

• i-Bu2AlH
• NaBH4 • Li(EtO)3AlH
• LiAlH4 • NaBH4, CeCl3 LiAlH4
• i-Bu2AlH • SmI2 LUCHE
• Et3SiH, TFA

• TsNHNH2, then NaBH3CN

• N2H4, KOH WOLFF–KISHER
• Zn(Hg), HCl CLEMMENSEN
• RSH, then Ni(Ra)

• TsCl, then [H]

• R’OH → R’Hal,
then Bu3SnH

COMMON REDUCING AGENTS

SmI2 (samarium iodide)
LiAlH4 LITHIUM ALUMINIUM
HYDRIDE (LAH)
NaBH4 SODIUM BOROHYDRIDE Selective reducing agent for
carbonyl compounds and halides in
Non-selective reagent for hydride transfer reductions. Reduces aldehydes and ketones to corresponding alcohols. the presence of esters and
Reacts with carboxylic acids, esters, lactones, anhydrides, Sodium borohydride is not reactive to esters, epoxides, carboxylic acids.
amides and nitriles, converting them into alcohols and lactones, carboxylic acids, nitro compounds and nitriles, but
amines. Ketones, aldehydes, epoxides, alkyl halides are also reduces acyl chlorides. In combination with CeCl3 allows for BH3·L (borane complexes)
reduced with lithium aluminium hydride. selective reductions of α,β-unsaturated carbonyls without Reduce carboxylic acids in the
reacting with С=С-bonds. presence of esters, amides and
halides.
LiBH4
DIISOBUTYLALUMINIUM HYDRIDE
LITHIUM BOROHYDRIDE i-Bu2AlH (DIBAL, DIBALH, DIBAl-H) AlH3 (aluminium hydride, alane)
Powerful reducing agent, which
Allows for selective reduction of esters in the presence of Reduces esters and amides (also Weinreb amides) to reacts with acids, esters, amides,
carboxylic acids, amides and nitriles. Also reacts with corresponding aldehydes. Nitriles are reduces to aldehydes nitriles, aldehydes, ketones, acyl
aldehydes, ketones and epoxides. too via imine formation step. chlorides and others.

2015 ПОД ТЯГОЙ

ORGCHEM.BY
License: Creative Commons BY-NC-ND
Photo: W. Oelen C bnd