16307-59-8Relevant academic research and scientific papers
Regioselective palladium-catalyzed synthesis of β-arylated primary allylamine equivalents by an efficient Pd-N coordination
Olofsson,Sahlin,Larhed,Hallberg
, p. 544 - 549 (2001)
A highly regioselective Heck arylation, utilizing aryl triflates and a palladium/dppf catalytic system, can be performed at the internal, β-carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction times and, in the case of Boc-protected allylamides, to improve the yields of two electron-poor aryl triflates.
Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines
Ding, Hao,Huang, Panyi,Jin, Can,Su, Weike,Sun, Bin,Yan, Zhiyang,Zhao, Haiyun
supporting information, (2021/10/29)
An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.
Preparation method of fused ring compound containing indole skeleton
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Paragraph 0036-0037, (2021/06/26)
The invention discloses a preparation method of a fused ring compound containing an indole skeleton. The preparation method comprises the following steps: carrying out intramolecular Heck reaction under the action of a palladium catalyst, a ligand, an add
Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides
Cabré, Albert,Romagnoli, Elia,Martínez-Balart, Pol,Verdaguer, Xavier,Riera, Antoni
supporting information, p. 9709 - 9713 (2019/11/19)
The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.
Hypervalent iodine(III)-Mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids
Kiyokawa, Kensuke,Yahata, Shunsuke,Kojima, Takumi,Minakata, Satoshi
supporting information, p. 4646 - 4649 (2015/01/09)
A novel oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C-O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C-N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I-N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.
N-bromoimide/DBU combination as a new strategy for intermolecular allylic amination
Wei, Ying,Liang, Fushun,Zhang, Xintong
supporting information, p. 5186 - 5189 (2013/11/06)
Allylic amination reactions of alkenes, with an NBP (N-bromophthalimide) or NBS (N-bromosuccinimide)/DBU combination, were developed, in which both internal and external nitrogen nucleophiles can be installed directly. Dual activation of NBS or NBP by DBU leads to more electrophilic bromine and more nucleophilic nitrogen atoms simultaneously. This protocol may provide a novel and complementary access to allylic amination under mild conditions.
Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions
Fort, Diego A.,Woltering, Thomas J.,Nettekoven, Matthias,Knust, Henner,Bach, Thorsten
supporting information, p. 2989 - 2991 (2013/05/09)
Intramolecular [2+2] photocycloaddition reactions of diversely substituted N-Boc protected 4-(allylaminomethyl)-2(5H)-furanones resulted in rigid products (53-75%) with three spatially defined positions for further functionalisation. The Royal Society of Chemistry.
Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched β-arylethylamines
Robertson, Jeremy,Palframan, Matthew J.,Shea, Stephen A.,Tchabanenko, Kirill,Unsworth, William P.,Winters, Chase
experimental part, p. 11896 - 11907 (2009/04/05)
5-exo Cyclisation of vinyl-, aryl- and alkyl-radicals onto the aryl group of arylcarboxamides is followed by β-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate
Synthesis, radiolabelling and confocal fluorescence microscopy of styrene-derivatised bis(thiosemicarbazonato)zinc and -copper complexes
Holland, Jason P.,Barnard, Peter J.,Bayly, Simon R.,Betts, Helen M.,Churchill, Grant C.,Dilworth, Jonathan R.,Edge, Ruth,Green, Jennifer C.,Hueting, Rebekka
experimental part, p. 1985 - 1993 (2009/03/11)
The synthesis of zinc(II) and copper(II) complexes of an unsymmetrical bis(thiosemicarbazonato) ligand containing a reactive styrene group are reported. The compounds have been characterised by a range of techniques including reverse-phase HPLC, cyclic vo
Potential GabaB Receptor Antagonists. V. The Application of Radical Additions to Styrenes to Produce 2-Hydroxysaclofen
Abbenante, Giovanni,Prager, Rolf H.
, p. 1791 - 1800 (2007/10/02)
3-Amino-2-(4-chlorophenyl)-2-hydroxypropanesulfonic acid (2-hydroxysaclofen), and its 2-phenyl analogue have been synthesized by three methods.Two involve the oxygen-catalysed free radical addition of bisulfite to the corresponding 3-aminopropene or 3-pht
