ArticleThe Journal of organic chemistry2013
Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Oxidative Cyclization of Sulfamates onto Pendant Alkenes.Organic letters · 2020Article
- Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.Journal of the American Chemical Society · 2016Article
- Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.Organic chemistry frontiers : an international journal of organic chemistry · 2016Article
- Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.ACS catalysis · 2016Article
- Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.Advanced synthesis & catalysis · 2015Article
- The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- CarboniumChemical science · 2013Article
- Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.The Journal of organic chemistry · 2013Article
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Abstract
The stereochemical course of the amidopalladation of alkenes has important implications for the development of enantioselective Pd-catalyzed "Wacker-type" oxidative amidation of alkenes. We have recently shown that the addition of base (Na2CO3) can alter the stereochemical course of amidopalladation in the (IMes)Pd(TFA)2(H2O)-catalyzed aerobic oxidative amidation of alkene. In this study, the mechanism of (IMes)Pd(TFA)2(H2O)-catalyzed oxidative heterocyclization of (Z)-4-hexenyltosylamide was investigated in the presence and absence of exogenous base Na2CO3. The results reveal two parallel pathways in the absence of base: a cis-amidopalladation pathway with turnover-limiting deprotonation of the sulfonamide nucleophile and a trans-amidopalladation pathway with turnover-limiting nucleophilic attack of sulfonamide on the coordinated alkene. The addition of base (Na2CO3) lowers the energy barrier associated with the proton transfer, leading to an overall faster turnover rate and exclusive cis-amidopalladation of alkene.
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