- Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
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In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
- Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
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supporting information
p. 5699 - 5703
(2019/08/01)
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- Palladium-Catalyzed meta-C-H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group
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The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including 1H NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.
- Fang, Siqiang,Wang, Xiaobing,Yin, Fucheng,Cai, Pei,Yang, Huali,Kong, Lingyi
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supporting information
(2019/03/19)
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- Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis
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A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.
- Akram, Manjur O.,Mali, Pramod S.,Patil, Nitin T.
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supporting information
p. 3075 - 3078
(2017/06/23)
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- Efficient double bond migration of allylbenzenes catalyzed by Pd(OAc) 2-HFIP system with unique substituent effect
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A novel catalyst system of Pd(OAc)2-HFIP induces double-bond migration of allylbenzenes under mild conditions with low catalytic loading to afford 1-propenylbenzenes. The reaction shows a unique substituent effect that is highly dependent on the distance of substituents from the allylic moiety. Thus, the reactivity of substrates bearing a methyl group is ordered in para > meta > ortho, whereas it is entirely reversed as ortho > meta > para for methoxy and chloro substituents.
- Nishiwaki, Nagatoshi,Kamimura, Ryuichiro,Shono, Kimihiro,Kawakami, Toshihiko,Nakayama, Katsuhisa,Nishino, Kohei,Nakayama, Takayuki,Takahashi, Keisuke,Nakamura, Aki,Hosokawa, Takahiro
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supporting information; experimental part
p. 3590 - 3592
(2010/08/19)
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- Phosphazene base-promoted halogen-zinc exchange reaction of aryl iodides using diethylzinc
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The use of catalytic t-Bu-P4 base dramatically improved the performance of halogen-zinc exchange of aryl iodides, and the arylzinc derivatives were functionalized under copper-free reaction conditions. The Royal Society of Chemistry 2006.
- Ueno, Masahiro,Wheatley, Andrew E. H.,Kondo, Yoshinori
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p. 3549 - 3550
(2008/09/19)
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- Intermolecular heck-type coupling of aryl iodides and allylic acetates
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(Chemical Equation Presented) A palladium-catalyzed arylation of allylic acetates followed by β-acetoxy elimination was shown to produce Heck-type coupling products. Optimal reaction conditions employed ligand-free palladium on carbon in the presence of tetrabutylammonium chloride, a trialkylamine base, and water.
- Mariampillai, Brian,Herse, Christelle,Laufens, Mark
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p. 4745 - 4747
(2007/10/03)
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- Direct Allylation of Aromatic Compounds with Allylic Chloride using the Supported Reagents System ZnCl2/SiO2-K2CO3/Al2O3
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Although the reaction of aromatic compounds with allylic chlorides using ZnCl2/SiO2, gives 2-chloro-1-arylalkanes accompanied with diarylalkanes, similar reaction using ZnCl2/SiO2-K2CO3/Al2O3 produces the monoallylated compound as the major product in good yield.
- Kodomari, Mitsuo,Nawa, Satoru,Miyoshi, Tadahiro
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p. 1895 - 1896
(2007/10/02)
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- Tandem Cyclization-Cycloaddition Reaction of Rhodium Carbenoids. Studies Dealing with Intramolecular Cycloadditions
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A series of 5-alkenyl-1-diazo-2,5-pentanediones, when treated with a catalytic quantity of rhodium(II) acetate, were found to give cycloadducts derived from the intramolecular trapping of a carbonyl ylide intermediate.Tethers of three or four methylenes r
- Padwa, Albert,Hornbuckle, Susan F.,Fryxell, Glen E.,Zhang, Zhijia J.
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p. 5747 - 5757
(2007/10/02)
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- Octahedral metal carbonyls LXV. Olefin isomerization in (2-allylphenyldiphenylphosphine)tetracarbonyltungsten(0)
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The stepwise displacement of pip (=piperidine) from cis-(pip)2W(CO)4 by 2-allylphenyldiphenylphosphine (adpp) affords cis(η3-adpp)W(CO)4 (1) when the cis-(pip)(η1-adpp)W(CO)4 intermediate (2; adpp is P-bonded) is isolated and purifie
- Wang, I-Hsiung,Dobson, Gerard R.
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- Intramolecular Ring Closure Reactions of Cyclopropene Derivatives as a Method for Synthesizing Novel Tricyclic Ring Compounds
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The thermal and photosensitized reactions of several 4-(methyldiphenylcyclopropenyl)-1-butenes have been studied.The thermolysis of these systems gave substituted tricyclo2,7>heptanes in good yield.The formation of this ring system invo
- Padwa, Albert,Rieker, William F.,Rosenthal, Robert J.
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p. 1353 - 1360
(2007/10/02)
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- UMPOLUNG OF REACTIVITY OF ALLYLSILANE, ALLYLGERMANE, AND ALLYLSTANNANE VIA THEIR REACTION WITH THALLIUM (III) SALT: A NEW ALLYLATION REACTION FOR AROMATIC COMPOUND
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A new direct allylation of the aromatic compound has been developed.A combination of allylsilane, allylgermane, or allylstannane and thallium (III) trifluoroacetate gave rise to an allyl cationic species which was allowed to react with an aromatic compound, a nucleophile, to give allylation product(s) in good yields.
- Ochiai, Masahito,Arimoto, Masao,Fujita, Eiichi
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p. 4491 - 4494
(2007/10/02)
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