1439384-16-3Relevant academic research and scientific papers
Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
Vinoth, Perumal,Karuppasamy, Muthu,Vachan,Muthukrishnan, Isravel,Maheswari, C. Uma,Nagarajan, Subbiah,Pace, Vittorio,Roller, Alexander,Bhuvanesh, Nattamai,Sridharan, Vellaisamy
, (2019/05/08)
A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.
Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes
Sze, Ella Min Ling,Koh, Ming Joo,Tjia, Yen Min,Rao, Weidong,Chan, Philip Wai Hong
, p. 5558 - 5565 (2013/07/04)
A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement and Br?nsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones efficiently is reported. The reactions proceed rapidly under mild and operationally straightforward conditions for a wide variety of aldehyde substrates containing electron-withdrawing, electron-donating, and sterically demanding functional groups and afforded the corresponding benzo-fused azaheterocyclic products in moderate to excellent yields.
