53810-72-3Relevant academic research and scientific papers
Iodine-Catalyzed Diels-Alder Reactions
Arndt, Thiemo,Wagner, Philip K.,Koenig, Jonas J.,Breugst, Martin
, p. 2922 - 2930 (2021)
The Diels-Alder cycloaddition is the most popular pericyclic reaction with numerous applications in synthesis and catalysis. We now demonstrate that we can perform this reaction under mild and metal-free conditions relying on molecular iodine as the catalyst. Cycloadditions with cyclohexadiene, cyclopentadiene, or isoprene with various dienophiles can be performed typically within minutes in moderate to good yields and high endo selectivity. The mechanistic studies including kinetic and DFT investigations clearly indicate a halogen-bond activation and rule out other modes of activation. Furthermore, iodine performs equally well as typical metallic Lewis acids like AlCl3, SnCl4, or TiCl4.
The Catalytic Diels-Alder Reaction Using Combined Catalyst System of Diphenyltin Sulfide or Lawesson's Reagent and Silver Perchlorate
Mukaiyama, Teruaki,Watanabe, Kimitoshi,Shiina, Isamu
, p. 1 - 2 (2007/10/02)
Catalytic Diels-Alder reaction between several 1,3-dienes and α,β-unsaturated ketones are effectively promoted by the combined use of diphenyltin sulfide (Ph2Sn=S) and silver perchlorate or Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-dipho
