Carbonylative coupling of organozinc reagents in the presence and absence of aryl iodides: synthesis of unsymmetrical and symmetrical ketones

Trans-chelating ligands in palladium-catalyzed carbonylative coupling and methoxycarbonylation of aryl halides

“…This transformation can be successfully realized through the three-component reaction of an aromatic electrophile (typically, aryl iodides, bromides, chlorides or triflates), carbon monoxide and an organometallic nucleophile from the standard arsenal of the cross-coupling reagents, such as organotin [10,11] [12], organoaluminum [13,14], organosilicon [15,16] and organoboron [17][18][19]. Of course, the latter reagent is more attractive for the everyday use due to its great stability, availability and long shelf-life.…”

Oxidative Carbonylation Reactions: Organometallic Compounds (RM) or Hydrocarbons (RH) as Nucleophiles

“…Subsequently, Jackson et al reported the palladiumcatalyzed oxidative carbonylation of organozinc reagents using O 2 as the oxidant (Scheme 8). [58] This reaction produced symmetric ketones in moderate to high yields, and avoided the requirement of stoichiometric amounts of metal compounds.…”

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

“…It should be noted that the problems with methanolysis of the SEM-ketone adducts, such as 21 and 23, were overcome by double oxidation of the deprotected benzaldehyde adduct 19, therefore allowing the synthesis of b-keto-a-amino acid 20 (entry iii). 20 A more demanding electrophile such as diethyl chlorophosphate could also be employed. Reaction of organolithium 12d with diethyl chlorophosphate delivered a good yield of the phosphonate 34 (Scheme 2), although reduced reaction times were required to minimise side reactions.…”