55487-53-1Relevant academic research and scientific papers
A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air
Kundu, Gourab,Rissanen, Kari,Schoenebeck, Franziska,Sperger, Theresa
supporting information, p. 21930 - 21934 (2020/10/02)
We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.
Synthesis of α-Chlorolactams by Cyanoborohydride-Mediated Radical Cyclization of Trichloroacetamides
Coussanes, Guilhem,Jakobi, Harald,Lindell, Stephen,Bonjoch, Josep
, p. 8151 - 8156 (2018/05/30)
A cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of α-chlorolactams (mono- and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.
Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes
Ohmura, Naoya,Nakamura, Asami,Hamasaki, Akiyuki,Tokunaga, Makoto
supporting information; experimental part, p. 5042 - 5045 (2009/05/07)
Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
, p. 2874 - 2879 (2008/02/03)
A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.
Indirect Electroreductive Cyclisation of N-Allylic and N-Propargylbromo Amides and o-Bromoacryloylanilides using Nickel(II) Complexes as Electron-transfer Catalysts
Ozaki, Shigeko,Matsushita, Hidenori,Ohmori, Hidenobu
, p. 2339 - 2344 (2007/10/02)
Nickel(II) complex-catalysed indirect electroreduction of N-allylic and N-propargyl-α-bromo amides and o-bromoacryloylanilides gave the corresponding 5-membered lactams.The product distribution was affected by the ability of the solvent to donate hydrogen atom.The electroreduction of N-allyl-N-(bromoacetyl)toluene-p-sulfonamide 1a in DMF and acetonitrile yielded as main product the 4-methylpyrrolidinone 2a (41percent) and the 4-(bromomethyl)pyrrolidinone 3a (33percent), respectively.On addition of 2 mol equiv. of a hydrogen-atom donor (Ph2PH) to the reaction of bromo amide 1a in acetonitrile, compound 1a provided compound 2a (58percent) as the sole cylised product.
CYCLIZATION OF α-HALOAMIDE WITH INTERNAL DOUBLE BOND BY USE OF THE LOW-VALENT METAL COMPLEX
Mori, Miwako,Oda, Izumi,Ban, Yoshio
, p. 5315 - 5318 (2007/10/02)
The α-haloamide having internal double bond was allowed to react with a catalytic amount of Pd(PPh3)4 in the presence of proton sponge to produce a cyclized product in a fairly good yield possibly through the intermediation of ?-alkylmetal complex althoug
