The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)−acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX−acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX− acetonitrile complex as a substrate under mild conditions is also described.
The stereoselective synthesis of cis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) from O-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone–acetonitrile complex (EBX–MeCN) is reported herein. The reaction was performed under mild conditions...
The synthesis of cis-β-amidevinyl
benziodoxolones
from the ethynyl benziodoxolone–chloroform complex and sulfonamides
is reported. Evidence indicates that highly reactive unsubstituted
ethynyl benziodoxolone undergoes Michael addition of sulfonamides,
including sterically demanding acyclic amino acid derivatives. The
synthesis of selectively deuterated cis-β-amidevinyl
benziodoxolones and investigation of ethynyl-λ3-iodane
reactivity are also described.
Ynamides
are versatile building blocks in organic synthesis. However,
the synthesis of amino acid-derived ynamides is difficult but in high
demand. Herein, we disclose the copper-catalyzed Csp-N coupling of
sulfonamide, including amino acid and peptide derivatives, to give
ynamides by using alkynyl benziodoxolones with broad functional group
tolerance under mild reaction conditions. The electron-rich bipyridine
as a ligand and ethanol as solvent were used for the success of this
reaction. The usefulness of the obtained amino acid-derived ynamide
as building block was showcased by further derivatization to unique
amino acid derivatives. A control experiment to elucidate the mechanistic
insight was also described.
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