Author Topic: Reference Requests  (Read 403 times)

Sedit

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Reference Requests
« on: May 10, 2009, 04:46:03 AM »
Quote
Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes

Sherry R. Chemler and Peter H. Fuller
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The de nouvo synthesis of small organic heterocyclic molecules has benefited from recent protocols for copper-facilitated additions of heteroatoms to alkenes, alkynes and arenes. This tutorial review summarizes a number of these recent contributions. al catalysts. The current understanding of the mechanisms of these reactions is presented. This review should be of interest to chemists Copper salts can facilitate bond formations due to their ability to serve as Lewis acids, oxidizing agents and transition metinvolved in the synthesis of heterocycles and those investigating transition metal facilitated reactions.
http://www.rsc.org/publishing/journals/CS/article.asp?doi=b607819m


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If anyone is able to pull up this Chemical Society Reviews paper it will be very helpful. I have been lookng into aminomercuration and a few things I have seen suggest Cu salts as a semi replacement for this form of organometallic reaction. It appeared almost as though its was a wacker reaction using NH3 instead of O2...... God lets hope ;D

I just want to get more information on the use of Copper in the addition to alkenes.


« Last Edit: October 25, 2010, 06:54:39 PM by Enkidu »
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Sedit

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Copper-Catalyzed Intermolecular Hydroamination of Alkenes
« Reply #1 on: May 10, 2009, 06:04:23 PM »
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Copper-Catalyzed Intermolecular Hydroamination of Alkenes

Regioselective additions of arylsulfonamides to vinylarenes, norbornene, and cyclohexadiene were achieved using a copper?diphosphine catayst under mild reaction conditions. These processes appear to be ligand-accelerated.


I may just merge this with the other request as to lump up all the references of this sort into the same area.
But seen here it does appear that copper may prove it self useful in aminating terminal Pi bonds. The reagents may look a little overwhelming but it does not mean it can't be performed under more accessible conditions. Im looking into this because of coppers ability to form complexes with amines and want to see what use it can be put to.
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Enkidu

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Re: Request:Copper facilitated addition of heteroatoms to alkenes, alkynes
« Reply #2 on: June 18, 2009, 09:56:08 PM »
sorry, didn't see this

Sedit

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Re: Request:Copper facilitated addition of heteroatoms to alkenes, alkynes
« Reply #3 on: June 18, 2009, 11:52:01 PM »
Thank you much Enkidu. It would be nice to find away around huge amounts of mercury for hydroamination reactions.
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Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
« Reply #4 on: August 09, 2009, 10:10:38 PM »
http://www3.interscience.wiley.com/journal/114279707/abstract

Abstract
Oxidation of series of various primary and secondary alcohols to corresponding carbonyl compounds with ammonium persulfate in aqueous media was described. No over oxidation of primary alcohols to carboxylic acids and secondary alcohols to esters was observed. Under such conditions benzoin was converted to benzoic acid.

I wouldn't mind reading this.. since ammonium persulfate can be produced easily, while acetaldehyde, and the others cannot.
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Re: Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
« Reply #5 on: August 09, 2009, 10:18:47 PM »
Sorry I don't have your reference but by any chance have you tryed adding some Ethanol to the black Mn(IV)sulfate slug ;). If its acetaldahyde your after you may be in for a plesent smelling suprise ::)
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Re: Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
« Reply #6 on: August 10, 2009, 12:19:15 AM »
I have, and there will be pictures to show the color change. I also bubbled the "gas" that formed into ammonia and hopefully something will be crystallizing soon.
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java

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Re: Copper-Catalyzed Intermolecular Hydroamination of Alkenes
« Reply #7 on: August 17, 2009, 04:36:43 PM »

Copper-Catalyzed Intermolecular Hydroamination of Alkenes
Jason G. Taylor, Neil Whittall,† and King Kuok (Mimi) Hii
Org. Lett. 2006, 8 (16), pp 3561–3564
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java

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Re: Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
« Reply #8 on: August 17, 2009, 04:39:34 PM »
Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
Gholam Hassan Imanzadeh, Mohammad R. Zamanloo, Yaghoob Mansoori, Ali Khodayari
Chinese Journal of Chemistry Volume 25, Issue 6 , Pages836 - 838. 2007
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Re: Aqueous Media Oxidation of Alcohols with Ammonium Persulfate
« Reply #9 on: August 17, 2009, 06:18:22 PM »
Thank you very much :D
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akcom

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someone with access to refs?
« Reply #10 on: August 20, 2009, 01:30:51 AM »
Could someone please post the following ref:
Inorg. Chem., 2007, 46 (6), pp 1903–1909

java

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Re: someone with access to refs?
« Reply #11 on: August 20, 2009, 04:21:08 AM »
Recent Progress in Wacker Oxidations:  Moving toward Molecular Oxygen as the Sole Oxidant
Candace N. Cornell and Matthew S. Sigman
Inorg. Chem. 2007, 46 (6), pp 1903–1909


By chamula

Abstract
Wacker oxidations, the conversion of terminal olefins to methyl ketones with Pd(II) catalysts, have seen widespread use in synthetic applications. Standard synthetic Wacker conditions use catalytic PdCl2 with stoichiometric CuCl under an aerobic atmosphere in a mixed-solvent system of N,N-dimethylformamide and H2O. Though much attention has been directed toward elucidating the rate-determining step and the mechanism of nucleopalladation, the assumption that Cu does not participate in this portion of the catalytic cycle has recently been called into question based on an isolated Pd/Cu bimetallic species and the influence of Cu on product selectivity. Fortunately, recent advancements have been made toward the elimination of Cu additives, thereby alleviating these issues. Success in this area has come from the application of information gained in studying other direct-O2-coupled Pd(II) oxidation systems, including ligand modulation, something which could not be achieved in the presence of Cu. The developments in peroxide-mediated and direct-O2-coupled Wacker oxidations are highlighted herein.
« Last Edit: September 13, 2010, 04:02:26 PM by java »
¡Prefiero morir de pie que vivir siempre arrodillado!.Emiliano ZapataIt is better to die on your feet than to live on your knees!.......

2bfrank

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Anyone access this partular
« Reply #12 on: August 20, 2009, 03:51:17 PM »
  J. Org. Chem. 2004, 69, 6907-6908

 The First Conversion of Primary Alkyl
Halides to Nitroalkanes under Aqueous
Medium

I am aware that it does not list lower nitroparaffins, but compares the traditional usage of DMF, DMSO, AgNO2, and has got me wondering... Apparently they use 4 X eq of AgNO2 with respect to alkyl bromide.


2b

No probs
The article only has this number associated -  10.1021/jo049048b
and WTF does partular mean other than a late night and slightly visually impaired.. It meant to read Particular..
« Last Edit: August 21, 2009, 12:14:00 AM by 2bfrank »

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Re: Anyone access this partular
« Reply #13 on: August 21, 2009, 01:10:17 AM »
The First Conversion of Primary Alkyl Halides to Nitroalkanes under Aqueous Medium
Roberto Ballini,* Luciano Barboni, and Guido Giarlo
J. Org. Chem. 2004, 69 (20), pp 6907–6908


By chamula


Abstract
Primary nitroalkanes and ?,?-dinitroalkanes can be easily obtained in aqueous medium by reaction of the corresponding halo derivatives with silver nitrite. The procedure works well with both alkyl bomide and alkyl iodide and proceeds in satisfactory to good yields even in the presence of other functionalities, minimizing the formation of the undesired alkyl nitrites.
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2bfrank

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Re: Anyone access this partular
« Reply #14 on: August 21, 2009, 03:32:53 AM »
Thank you Java, and for the many others I have learnt lots from, and I dare say their is likely to be more to come... The title of that paper, sort of warranted a look...I am far from accepting this paper as a possible route to prepping nitroparaffins of interest,  but..I am beginning to see the importance of experimentation, and to really think about the players, their states, and the media they are playing in..Rather than somewhat blindly accepted the work of others.. Thanks again..

2b

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Re: Copper-Catalyzed Intermolecular Hydroamination of Alkenes
« Reply #15 on: September 09, 2009, 05:46:15 AM »
that's a sulfonamide i don't see the analogy since it has different electronic properties.
a more apt term for this rxn would be hydroamidation.