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Influence of Catalyst Structure and Reaction Conditions on anti ‐ versus syn ‐Aminopalladation Pathways in Pd‐Catalyzed Alkene Carboamination Reactions of N ‐Allylsulfamides

By Ryan M. Fornwald, Jonathan A. Fritz and John P. Wolfe

Abstract

The Pd‐catalyzed coupling of N ‐allylsulfamides with aryl and alkenyl triflates to afford cyclic sulfamide products is described. In contrast to other known Pd‐catalyzed alkene carboamination reactions, these transformations may be selectively induced to occur by way of either anti ‐ or syn ‐aminopalladation mechanistic pathways by modifying the catalyst structure and reaction conditions. A constructive approach : A concise, efficient approach has led to the synthesis of cyclic sulfamides by using Pd‐catalyzed alkene carboamination reactions of N ‐allylsulfamides (see picture; OTf=triflate, RuPhos=2‐dicyclohexylphosphino‐2′,6′‐diisopropoxybiphenyl, X‐phos=2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropylbiphenyl). The mechanism of these transformations is highly dependent on the catalyst structure and reaction conditions. The reactions can be induced to proceed selectively through either syn ‐ or anti ‐aminopalladation pathways under appropriate conditions

Publisher: WILEY‐VCH Verlag
Year: 2014
DOI identifier: 10.1002/chem.201402258
OAI identifier: oai:deepblue.lib.umich.edu:2027.42/107505
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