- Synergistic Copper-Catalyzed Reductive Aminocarbonylation of Alkyl Iodides with Nitroarenes
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We have developed a Cu-catalyzed reductive aminocarbonylation of alkyl iodides using nitroarenes as the nitrogen source. The reaction proceeds with a single copper catalyst playing dual roles of synergistically mediating both carbonylation of alkyl iodide
- Zhao, Siling,Mankad, Neal P.
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supporting information
p. 10106 - 10110
(2019/12/24)
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- Organic ligand-free carbonylation reactions with unsupported bulk Pd as catalyst
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Herein, surprising results for bulk Pd-catalyzed carbonylation reactions are presented. Three types of carbonylation reactions can be realized efficiently under organic ligand-free conditions, namely, hydroaminocarbonylation of olefins, aminocarbonylation of aryl iodides and oxidative carbonylation of amines, which almost cover all the known mechanisms in carbonylation reactions. Notably, the bulk Pd catalyst system exhibited better catalytic activity than the classical homogeneous PdCl2/(2-OMePh)3P catalyst system. This study will create a momentous and new field of green carbonylation reactions.
- Liu, Shujuan,Wang, Hongli,Dai, Xingchao,Shi, Feng
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supporting information
p. 3457 - 3462
(2018/08/06)
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- Selective Palladium-Catalyzed Aminocarbonylation of Olefins to Branched Amides
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A general and efficient protocol for iso-selective aminocarbonylation of olefins with aliphatic amines has been developed for the first time. Key to the success for this process is the use of a specific 2-phosphino-substituted pyrrole ligand in the presence of PdX2(X=halide) as a pre-catalyst. Bulk industrial and functionalized olefins react with various aliphatic amines, including amino-acid derivatives, to give the corresponding branched amides generally in good yields (up to 99 %) and regioselectivities (b/l up to 99:1).
- Liu, Jie,Li, Haoquan,Spannenberg, Anke,Franke, Robert,Jackstell, Ralf,Beller, Matthias
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supporting information
p. 13544 - 13548
(2016/10/21)
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- Selective formation of α,ω-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates
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The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω- ester amides, whilst reactions in THF give N-phenylpyrrolidine.
- Jimenez-Rodriguez, Cristina,Nunez-Magro, Angel A.,Seidensticker, Thomas,Eastham, Graham R.,Furst, Marc R. L.,Cole-Hamilton, David J.
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p. 2332 - 2339
(2014/07/22)
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- Selective palladium-catalyzed aminocarbonylation of olefins with aromatic amines and nitroarenes
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Various olefins can be smoothly transformed in the presence of a Pd-based catalyst system and (hetero)aromatic amines or nitroarenes to synthetically interesting amides in good yields and often with high regioselectivity (see scheme). Combining this atom-efficient procedure with established functionalizations of the resulting products allows the efficient preparation of quinolines. Copyright
- Fang, Xianjie,Jackstell, Ralf,Beller, Matthias
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supporting information
p. 14089 - 14093
(2014/01/06)
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- Non-Lactone Carbocyclic and Heterocyclic Antagonists and Agonists of Bacterial Quorum Sensing
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Compounds which modulate quorum sensing in quorum sensing bacteria. Compounds of the invention inhibit quorum sensing and/or activate quorum sensing in various bacteria. Compounds that inhibit quorum sensing are particularly useful for inhibition of detri
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Page/Page column 21-22
(2011/04/14)
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- A novel approach for the direct conversion of alkylsulfonyl derivatives into alkylcarbonyl derivatives via tin-free radical carbonylation
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A novel radical approach for the direct conversion of RSO2X into RCOX in a single step is devised; the present approach is very simple, highly efficient, and minimizes formation of by-product. The Royal Society of Chemistry.
- Kim, Sangmo,Lim, Kyoung-Chan,Kim, Sunggak
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p. 4507 - 4509
(2008/04/01)
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- Catalytic one-pot synthesis of N-phenyl alkyl amides from alkene and aniline in the presence of cobalt on charcoal under carbon monoxide
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N-Phenyl alkyl amides were synthesized by the cobalt on charcoal-catalyzed one-pot reaction of alkene and aniline under carbon monoxide; this is the first heterogeneous catalytic formation of N-phenyl alkyl amides.
- Lee, Sang Ick,Son, Seung Uk,Chung, Young Keun
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p. 1310 - 1311
(2007/10/03)
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- Charge-directed conjugate addition reactions of silylated α-β- unsaturated amidate anions
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A variety of N-substituted α-silylated-α,β-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. β-Substituted acceptors were found to react only with reactive organolithium reagents while a β,β-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.
- Cooke Jr.,Pollock
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p. 7474 - 7481
(2007/10/02)
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- A Convenient Synthesis of Amides with 2-Halo-2,3-dihydro-1,3,4,2-oxadiazaphospholes as a New Condensing Agents
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Various amides, including some with bulky substituents, are prepared in good yields from free carboxylic acids and amines under mild conditions by a one-step method using new condensing agents 2-halo-2,3-dihydro-1,3,4,2-oxadiazaphospholes, especially 5-methyl-2-chloro-3-phenyl-2,3-dihydro-1,3,4,2-oxadiazaphosphole.
- Kimura, Hiroshi,Konno, Hidetoshi,Takahashi, Naomichi
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p. 327 - 329
(2007/10/02)
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