Neue Darstellungsmethode für Isonitrile

Multicomponent Reactions with Organoboron Compounds

“…Among the most widely used components for MCRs involving amines and carbonyls are the isocyanides (isonitriles) 26, which were initially used in the Passerini reaction [21] and more extensively in a series of MCRs introduced by Ugi (Scheme 7.4) [1,5,22]. The great effectiveness of isocyanides in MCRs is apparently a result of their remarkable balance between nucleophilic and electrophilic reactivity that enables them to be relatively unreactive towards carbonyl compounds but quite reactive with activated derivatives such as the corresponding iminium species.…”

Reaction of Carboxylic Acids with Isocyanides: A Mechanistic DFT Study

“…[1] In particular, it is the propensity of the terminal carbon atom to function both as a nucleophile and an electrophile (α-addition) that makes isocyanides extremely attractive starting materials for the generation of molecular diversity. [2] This distinctive behavior is exploited in popular transformations such as the Passerini [3] and Ugi [4] multicomponent reactions. Recently, Li and Danishefsky reported that, when subjected to high temperatures, isocyanides react with carboxylic acids to selectively afford N-formyl imides in good to excellent yields (Scheme 1).…”

The Four‐Component Reaction and Other Multicomponent Reactions of the Isocyanides

“…4 A systematic search for the most suitable dehydrating reagent revealed early on that phosgene 31 is excellent for this purpose. Later, when phosgene transportation was not allowed anymore, it was locally produced from triphosgene.…”