Rhodium(II,II) dimer as an efficient catalyst for aziridination of sulfonamides and amidation of steroids.
[reaction: see text] Unsaturated sulfonamides underwent direct intramolecular aziridination catalyzed by Rh(2)(OAc)(4) with PhI(OAc)(2) and Al(2)O(3) to give the corresponding aziridine products in excellent yields (up to 98%) and with good to excellent conversions. High turnovers (up to 1375) were achieved. The intermolecular rhodium-catalyzed amidation of cholesteryl acetate with PhI=NTs or PhI(OAc)(2)/NH(2)R as the nitrogen source exhibited both excellent regio- and alpha-selectivity (alpha/beta ratio up to 9:1).
Liang
Jiang-Lin
JL
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.
Yuan
Shi-Xue
SX
Chan
Philip Wai Hong
PW
Che
Chi-Ming
CM
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D019281:Dimerization; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
D000577:Amides; D013256:Steroids; D013449:Sulfonamides; D012238:Rhodium