The Schmidt reaction uses catalytic acid and hydrazoic acid to convert carboxylic acids, aldehydes, ketones, olefins, and 3° alcohols to amines, nitriles, amides, imines, and imines respectively. In the case of aldehydes, hydrazoic acid attacks the carbonyl group, to form a tetrahedral azidoalkanol intermediate. Water is expelled as nitrogen forms...

The synthesis of amides from amines and esters from alcohols with acyl halides or anhydrides in the presence of a base is known as the Schotten-Baumann reaction. The amine attacks the acyl halide, forming a tetrahedral intermediate that releases a halide ion. Deprotonation of the positively charged nitrogen affords the...

The Sonogashira cross-coupling reaction uses catalytic palladium, a copper(I)-salt, and a base to couple an organohalide and a terminal alkyne. The mechanism follows the expected oxidative addition-reductive elimination cycle, but the precise role of the Cu(I)-salt catalyst has not been fully elucidated. Good for small or large scale (>100g), this...

The Staudinger reaction uses a trivalent phosphorous compound such as triphenylphosphine, an organic azide, and water to make a primary amine. Triphenylphosphine first attacks the terminal nitrogen of the azide, creating a phosphazide intermediate, which undergoes a rearrangement to release nitrogen gas and form an iminophosphorane intermediate (also known as...

The Stille cross-coupling reaction uses a palladium catalyst to couple an organohalide and an organostannane. The mechanism follows the expected oxidative addition-reductive elimination. Reagents: Catalytic Palladium (Pd(PPh3)4, Pd(dba)2, etc.) Reactant: Organohalide, Organostannane Product: Coupled Product Type of Reaction: C-C Cross-Coupling Lab Tips Organostannanes are easy to work with as they...

The Strecker amino acid synthesis generates an α-amino acid from hydrogen cyanide, water, an aldehyde or ketone, and a 1° amine or ammonia. The carbonyl compound is first converted to an iminium ion, which is attacked by the cyanide ion to form an α-amino nitrile intermediate. Hydrolysis of the nitrile...