S and P
S bonds of thioamides and thiophosphonyl diamides into C
N and P
N bonds of N-sulfonyl amidines via interaction with iminoiodinanes
An azide-free approach toward N-sulfonyl amidines, including phosphorus-containing derivatives based on the reactions of thioamides and thiophosphonyl diamides with iminoiodinanes, was developed.
A practical and convenient approach for the highly stereoselective synthesis of N-sulfonyl amidines via a one-pot multi-component cascade reaction of sulfonyl azides, amines, water, and calcium carbide as an acetylene source has been developed.
Hydroxylamine hydrochloride-catalyzed transamidation of primary thioamides with primary and secondary amines via C(S)–N bond cleavage and formation has been reported.
A novel base-promoted olefin skeletal rearrangement strategy from para-quinone methides (p-QMs) and N-fluoroarenesulfonamides is reported, enabling direct nitrogen insertion of olefins to produce multiarylated (Z)-N-sulfonyl amidines.
Primary trifluoroborate-iminiums are transformed into N-sulfonyl amidines in an azide- and transition-metal-free C(sp2)–N bond-forming reaction under mild conditions. The mechanism was elucidated via NMR, mass spectrometry and DFT calculations.