Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH-transfer is likely to be first, followed by oxidation, but the reaction proceeds successfully in either order. A wide range of functional groups and biologically relevant compounds are tolerated. The use of AcO15NH4 affords 15N-labeled compounds.
Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers / Tota, Arianna; Zenzola, Marina; Chawner, Stephen J.; John Campbell, Sahra St; Carlucci, Claudia; Romanazzi, Giuseppe; Degennaro, Leonardo; Bull, James A; Luisi, Renzo. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - STAMPA. - 53:2(2017), pp. 348-351. [10.1039/c6cc08891k]
Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers
ROMANAZZI, Giuseppe;
2017
Abstract
Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH-transfer is likely to be first, followed by oxidation, but the reaction proceeds successfully in either order. A wide range of functional groups and biologically relevant compounds are tolerated. The use of AcO15NH4 affords 15N-labeled compounds.| File | Dimensione | Formato | |
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O-N-transfer-Sulfide_ChemCommun.pdf
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