Reaction Of Organic Halides Research Articles

ChemInform Abstract: A Historic Overview of the Metal‐Catalyzed Cross‐Coupling Reactions.

The main focus of this publication is the innovation of new synthetic reactions that can form various carbon–carbon bonds with high selectivity. The use of transition-metal-catalyzed cross-coupling reactions of organic electrophiles with organometallic nucleophiles started with the discovery of Kumada–Tamao–Corriu coupling in 1972—the reaction of organic halides and organomagnesium compounds under nickel catalysis. Combining fragments with a series of carbon centers into one segment, the transition-metal-catalyzed cross-coupling reactions have long been industrially utilized toward the synthesis of functional materials such as agricultural chemicals, pharmaceuticals, and polymers.

Radical Mechanisms in the Reaction of Organic Halides with Diiminepyridine Cobalt Complexes

The formally Co(0) complex LCo(N2) (L = 2,6-bis(2,6-dimethylphenyliminoethyl)pyridine) can be prepared via either Na/Hg reduction of LCoCl2 or hydrogenolysis of LCoCH2SiMe3. In the latter reaction, LCoH could be trapped by reaction with N≡CC6H4-4-Cl to give LCoN═CHC6H4-4-Cl. LCo(N2) reacts with many alkyl and aryl halides RX, including aryl chlorides, to give a mixture of LCoR and LCoX in a halogen atom abstraction mechanism. Intermediacy of free alkyl and aryl radicals is confirmed by the ring-opening of cyclopropylmethyl to crotyl, and the rearrangement of 2,4,6-tBu3C6H2 to 3,5-tBu2C6H3CMe2CH2, before binding to Co. The organocobalt species generated in this way react further with activated halides R′X (alkyl iodides; allyl and benzyl halides) to give cross-coupling products RR′ in what is most likely again a halogen abstraction mechanism. DFT studies support the proposed radical pathways for both steps. MeI couples smoothly with LCoCH2SiMe3 to give LCoI and CH3CH2SiMe3, but the analogous reaction of tB...

ChemInform Abstract: A Novel and Convenient Method for Trifluoromethylation of Organic Halides Using CF3SiR′3/KF/Cu(I) System.

Abstract Fluoride ion induced cross-coupling reaction of organic halides with trifluoromethyltrialkylsilanes takes place in the presence of Cu(I) salts under mild reaction conditions to give the corresponding trifluoromethylated products in high yields.

On the reaction of 4-chloromethylene-2,6-di-tert-buthylcyclohexa- 2,5-dien-1-one with P(III) acids esters

Proceeding with investigations on reactions of organic halides with aprotic reagents [1, 2], we pioneered in studying reactions of 4-chloromethylene2,6-di-tert-butylcyclohexa-2,6-dien-1-one I (chloromethylenequinone) with P(III) acids esters, such as triethyl phosphite IIа and ethyl diphenylphosphinite IIb. Phosphorylated ylides VII were established to be the main products of the reaction of chloromethylenequinone I with esters II in a 1:2 ratio. We suppose that ylide VII is formed by the following two-stage scheme: DOI: 10.1134/S1070363209010307

Improved Method for the Synthesis of Organic Diselenides from Organic Halides under Atmospheric Pressure

An improved approach to the synthesis of organic diselenides is reported. The process involves the reaction of organic halides with selenium, carbon monoxide, and water under atmospheric pressure in the presence of an inorganic base, sodium hydroxide, to afford organic diselenides in good yields.

Highly Efficient Water‐Promoted Allylation and Propargylation of Arylepoxides via Rearrangement‐Carbonyl Addition.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Tuning the Reactivity of Organotin(IV) by LiOH: Allylation and Propargylation of Epoxides via Redox Transmetalation.

In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl 2 -LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant.

Palladium‐Catalyzed Cross‐Coupling Reaction of Organic Halides with Grignard Reagents, Organolithium Compounds and Heteroatom Nucleophiles.

AbstractFor Abstract see ChemInform Abstract in Full Text.

ChemInform Abstract: Reactions of Organic Halides with Organometallic Compounds and Terminal Acetylenes Catalyzed by Palladium Complexes

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reactions of organic halides with organometallic compounds and terminal acetylenes catalyzed by palladium complexes

The results of the investigation of the cross-coupling of organometallic compounds and terminal acetylenes with organic halides catalyzed by transition metal complexes are generalized and analyzed. The influence of different factors on the rate and selectivity of catalytic cross-coupling is discussed. A detailed mechanism of the cross-coupling of Grignard reagents with organic halides is suggested. The cross-coupling reaction involving organotin compounds proceeds under very mild conditions in the presence of a ligand-free Pd catalyst. Examples of using catalytic cross-coupling of organic halides with organomagnesium, organozinc, and organotin compounds are presented.

ChemInform Abstract: Palladium‐Catalyzed Ring‐Forming Reactions of Organic Halides with Unsaturated Substrates and Carbon Monoxide

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Not for Synthesis Only: The Reactions of Organic Halides with Metal Surfaces

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reaction of organic halides with [Cu I(TMPA)CH 3CN]PF 6

Under mild conditions, the copper(I) complex [Cu I(TMPA)CH 3CN]PF 6 (TMPA=tris(2-pyridyl-methyl)amine), reacts stoichiometrically with benzyl and allyl halides, and α-halo-ketones to produce near quantitative yields of carbon-carbon reductively coupled products bibenzyls, diolefins or diketones, respectively. The copper complex acts as the halide acceptor and the copper(II) complex [Cu II(TMPA)X]PF 6 (XCl − or Br −) is also isolated. No firm mechanistic conclusions can be drawn, but the intermediacy of oxidatively added RX products, i.e. organo-Cu(II) or Cu(III), is suggested.

Reactions of organic halides with the carbonyl anions [M(CO)4]- (M = Rh, Ir). Crystal and molecular structure of [PPN][IrBr2(CO)2(CH2CO2Me)2] and of [PPN][Ir(CO)2(CH2CN)2] (PPN+ = [(Ph3P)2N]+)

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReactions of organic halides with the carbonyl anions [M(CO)4]- (M = Rh, Ir). Crystal and molecular structure of [PPN][IrBr2(CO)2(CH2CO2Me)2] and of [PPN][Ir(CO)2(CH2CN)2] (PPN+ = [(Ph3P)2N]+)Francesca Porta, Fabio Ragaini, Sergio Cenini, and Francesco DemartinCite this: Organometallics 1990, 9, 4, 929–935Publication Date (Print):April 1, 1990Publication History Published online1 May 2002Published inissue 1 April 1990https://doi.org/10.1021/om00118a006RIGHTS & PERMISSIONSArticle Views113Altmetric-Citations17LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (875 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

ChemInform Abstract: Reactions of Organic Halides with Olefins Under Ni(0)‐Catalysis. Formal Addition of Hydrocarbons to CC‐Double Bonds.

AbstractThe electron‐deficient olefins (I) are alkylated with the halides (II) in the presence of a Ni(0) catalyst generated in situ, forming the adducts (III).

ChemInform Abstract: Palladium‐Catalyzed Reaction of Organic Halides with Organotin Compounds Involving Olefin Insertion: Synthesis of 2,3‐Disubstituted Norbornanes.

ChemInform Abstract: Palladium‐Catalyzed Reaction of Organic Halides with Organotin Compounds Involving Olefin Insertion: Synthesis of 2,3‐Disubstituted Norbornanes.

Generation of cold free radicals by the reaction of organic halides with metal atoms produced by laser vaporization

Reactive Ba atoms are produced from a Ba rod by YAG laser vaporization in the throat of a seeded He supersonic jet expansion. As the expansion proceeds, the Ba atoms react with the seed gas, benzyl chloride. The reaction products, BaCl and benzyl radical, are observed substantially cooled downstream via laser-induced fluorescence.

Reactions of organic halides with olefins under Nio-catalysis. Formal addition of hydrocarbons to CC-double bonds

The reaction of various types of organic halides with electron deficient olefins under the influence of NiCl2 × 6 H2O in the presence of zinc and pyridine leads to formal addition products of hydrocarbons to CC-double bonds in good yield.

Reaction of organic halides with chlorotris(triphenylphosphine)cobalt(I).

Reaction of various types of organic halides with a monovalent cobalt complex, chlorotris (triphenylphosphine) cobalt (I) is described. Reaction of benzylic monohalides, dihalides and trihalides with CoCl (Ph3P)3 gave a coupling product with formation of a carbon-carbon single bond, double bond and triple bond, respectively, under mild and non-basic conditions. Dehalogenation of non-benzylic vicinal dihalides with the reagent took place cleanly to give an olefin in high yield. Reductive coupling of allylic halides using the reagent afforded regioselectively a 1, 5-diene with retention of the stereochemistry of the carbon-carbon double bond of the allylic halides used. By using this reaction, (E, E, E, E)-squalene was stereospecifically synthesized from (E, E)-farnesyl bromide. Reaction of halohydrins with CoCl (Ph3P)3 gave exclusively a ketone in the presence of an amine or olefin through an alkylcobalt intermediate. A 1, 2-hydrogen shift is involved in this reaction.

Reactions of organic halides with a trigonal pyramidal nickel(0) complex

The nickel(0) comlex [Ni(np 3)], np 3  tris(2-diphenylphinoethyl)amine, which has a trigonal pyramidal geometry in the solid state, readily reacts in solution with organic halides (CH 3I, C 2H 5Cl, C 3H 7Cl, C 6H 5Cl, C 6H 5Br, C 6H 5I and C 6H 5CH 2Cl) to give nickel(I) species with formula [NiX(np3)], (X  Cl, Br, I). Benezene, biphenyl, o-, m-, p-chlorobiphenyl are the other products from the reaction between the title complex and chlorobenzene.