Rhodium(II)-Catalyzed CH Insertions with {[(4-Nitrophenyl)sulfonyl]imino}phenyl-λ<sup>3</sup>-iodane

Article Article scientifique Article Rhodium(II)-Catalyzed CH Insertions with {[(4-Nitrophenyl)sulfonyl]imino}phenyl-λ<sup>3</sup>-iodane eng 1997 author Nageli Ivo 100482 author Baud Corine 29076 author Bernardinelli Gérald Hugues 24765 author Jacquier Yvan Daniel Michel 23777 author Moran Mary 90586 author Muller Paul 24995 1087-1105 10.1002/hlca.19970800407 0018-019X http://doi.wiley.com/10.1002/hlca.19970800407 The [Rh₂(OAc)₄]‐catalyzed decomposition of {[(4‐nitrophenyl)sulfonyl]imino}phenyl‐λ³‐iodane (NsN=IPh) resulted in formal insertions into CH bonds, activated by phenyl or vinyl groups, or by O‐substituents. Scope and limitations of the reaction were investigated. Yields of up to 84% were achieved in the most favorable cases. Yields were enhanced by electron‐releasing substituents and decreased by steric hindrance. Aziridination competed with allylic insertion with olefinic substrates. The insertion reaction proceeded with retention of configuration. With chiral RhII catalysts, a modest asymmetric induction was observed. A mechanism involving direct insertion by a Rh‐complexed nitrene into the CH bond is proposed. Dewey 540 36 Département de chimie organique 141 false Helvetica Chimica Acta 80 4 a579593e-b43f-4441-91bc-9f1db44aab0e Article (Published version) Restricted N-geli_et_al-1997-Helvetica_Chimica_Acta.pdf 1136988 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Rhodium(II)-Catalyzed CH Insertions with {[(4-Nitrophenyl)sulfonyl]imino}phenyl-λ³-iodane	Helvetica Chimica Acta			1997	310	0

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