Carbonyl groups undergo the sequential installation of two nucleophilic elements, halomethyl and fluoride moieties.
Due to the well known reactivity of C(O)–N functionalities towards canonical C1-homologating agents (e.g. carbenoids, diazomethane, ylides), resulting in the extrusion of the N-centered fragment en route to carbonyl compounds, formal C1-insertions within N–O bonds still remain obscure.
α-Substituted methylsulfinamide are prepared through the homologation of electrophilic N-sulfinylamines with Li-CHXY reagents.
The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithium halocarbenoids is reported.
This review summarises the reactivity and synthetic procedures of aryl and acyl isothiocyanates, a versatile reagent with multiple reactive centres.