- Iridium complex-linked porous organic polymers for recyclable, broad-scope photocatalysis of organic transformations
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Two rigid porous organic polymers (Ir-POP-1 and Ir-POP-2) were prepared from the coupling reactions of tetraphenylmethane tetraborate and two [Ir(ppy)2(dtbbpy)]+-based bitopic linkers and applied as heterogeneous visible-light photocatalysts for organic transformations. Ir-POP-2 was found to exhibit high catalytic activity for a wide range of organic reactions, which include Smiles-Truce rearrangement of alkyliodides, desulfurative conjugate addition to Michael acceptors, and aerobic oxidations of sulfides and arylboronic acids. For all the transformations, Ir-POP-2 could achieve heterogeneous photocatalytic efficiency that rivals that of the homogeneous prototype iridium complexes. This remarkably high photocatalytic performance has been attributed to the large pore size of the conjugated backbone. The new heterogeneous photocatalyst was also highly stable to achieve good recyclability for all the studied reactions and could be reused eight to nineteen times.
- Xu, Zi-Yue,Luo, Yi,Zhang, Dan-Wei,Wang, Hui,Sun, Xing-Wen,Li, Zhan-Ting
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supporting information
p. 136 - 143
(2020/01/21)
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- Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide
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A general and efficient method for the synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols and 3-amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).
- He, Tian,Gao, Wen-Chao,Wang, Wei-Kun,Zhang, Chi
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supporting information
p. 1113 - 1118
(2014/04/03)
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- Chemoselective intramolecular alkylation of the Blaise reaction intermediates: Tandem one-pot synthesis of exo -cyclic enaminoesters and their applications toward the synthesis of N -heterocyclic compounds
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The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.
- Kim, Ju Hyun,Shin, Hyunik,Lee, Sang-Gi
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experimental part
p. 1560 - 1565
(2012/04/04)
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- Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates
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Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of ω-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of ω-chloroalkyl nitriles give N-fused indoles. Georg Thieme Verlag Stuttgart · New York.
- Kim, Juhyun,Chun, Yusung,Shin, Hyunik,Lee, Sang-Gi
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experimental part
p. 1809 - 1817
(2012/08/08)
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- Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418
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A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.
- Wang, Youchu,Papamichelakis, Maria,Chew, Warren,Sellstedt, John,Noureldin, Razzak,Tadayon, Sam,Daigneault, Sylvain,Galante, Rocco J.,Sun, Jerry
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p. 1253 - 1260
(2013/01/03)
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- Efficient synthesis of β-amino-α,β-unsaturated carbonyl compounds
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A versatile and high-yielding procedure for the synthesis of β-enamino esters and β-enaminones is presented: in the presence of tetraethyl orthosilicate, a number of highly functional β-enamino esters were obtained; this method provided an alternative for the formation of β-amino-α,β-unsaturated carbonyl compounds with mild and functional group compatible reaction conditions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Zhao, Yuanhong,Zhao, Jingfeng,Zhou, Yongyun,Lei, Ze,Li, Liang,Zhang, Hongbin
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p. 769 - 772
(2007/10/03)
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- C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
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Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C1-symmetric bisphosphine ligands bound to transition metals.
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Page/Page column 22
(2008/06/13)
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- A Convenient and Effective Method for Synthesizing β-Amino-α ,β-Unsaturated Esters and Ketones
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A convenient and effective method for the preparation of β-amino-α, β-unsaturated esters and ketones has been developed through silica gel-catalyzed and solvent-free reactions of β-dicarbonylic compounds with ammonia and primary amines.
- Gao, Yuanhe,Zhang, Qihan,Xu, Jiaxi
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p. 909 - 916
(2007/10/03)
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- Enantioselective hydrogenation of tetrasubstituted olefins of cyclic β-(acylamino)acrylates
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Hydrogenation of a series of cyclic β-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic β-amino acid derivatives. Copyright
- Tang, Wenjun,Wu, Shulin,Zhang, Xumu
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p. 9570 - 9571
(2007/10/03)
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- BENTONITE K10 CLAY, AN EFFICIENT CATALYST FOR THE FORMATION OF NITROGEN DERIVATIVES
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Bentonite K10 clay has been used to catalyze the formation of enamino carbonyl derivatives, 2-methyl-1H-benzimidazoles, Hantzsch 1,4-dihydropyridines, Hantzsch pyridines, 2-substituted 1,3-diphenylimidazolidines, and tetrahydropyranylbenzazoles.
- Eynde, Jean Jacques Vanden,Mayence, Annie,Lor, Pascal,Haverbeke, Yves Van
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p. 387 - 392
(2007/10/02)
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- Fused cycloalkylimidazopyridines
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[6,7]-propylene-, -butylene- or -pentylene-fused imidazopyridin-4-amines that induce interferon (α) biosynthesis in human cells. Also disclosed are pharmaceutical compositions containing such compounds and methods of inducing interferon (α) biosynthesis and treating viral infections involving the use of such compounds.
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