- A soluble polymer-supported triflating reagent: a high-throughput synthetic approach to aryl and enol triflates.
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[reaction: see text] The high-yielding synthesis and application of the first example of a polymer-supported reagent for the preparation of trifluoromethanesulfonates (triflates) is described. This new reagent efficiently triflates aryl alcohols and lithi
- Wentworth,Wentworth Jr.,Mansoor,Janda
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- Aryl triflates and [11C]/(13C)carbon monoxide in the synthesis of 11C-/13C-amides
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Palladium(0)-mediated carbonylation reactions using aryl triflates, amines, and a low concentration of [11C]carbon monoxide were used in the syntheses of 13 11C-labeled amides. Lithium bromide was used as an additive to facilitate the reaction. The 11C-labeled products were obtained with decay-corrected radiochemical yields in the range of 2-63%. The radiochemical purity of the final products exceeded 98%. As an example, a reaction starting with 1.79 GBq [11C]carbon monoxide gave 0.38 GBq of LC-purified N-isopropyl-4-nitro-[11C]benzamide within 27 min from the start of the carbonylation reaction (54% decay-corrected radiochemical yield). The specific radioactivity of this compound was 191 GBq/μmol, 35 min after the end of a 10 μAh bombardment. N-Benzyliso-quinoline-1-(13C)carboxamide was prepared and analyzed by NMR for confirmation of the labeling position. The triflates 16, 20, 21, and 22 were synthesized from the corresponding alcohols and trifluoromethanesulfonic anhydride. The reference compounds 30a and 30b were prepared from the corresponding carboxylic acids and benzylamine. The other nine reference compounds 32a to 32i were synthesized from the respective acid chlorides and amines. The presented report shows that the sometimes more easily obtainable aryl triflates can be a useful alternative to the commonly used aryl halides in palladium(0)-mediated synthesis of 11C/13C-amides.
- Rahman, Obaidur,Kihlberg, Tor,Langstroem, Bengt
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- Palladium Catalysed Alkoxycarbonylation of Phenols to Benzoate Esters
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The methoxycarbonylation of aryl trifluoromethanesulphonates with CO and aliphatic alcohols is catalysed by Pd(OAc)2-1,3-bis(diphenylphosphino)propane in high yield at 70 deg C and ambient CO pressure.
- Dolle, Roland E.,Schmidt, Stanley J.,Kruse, Lawrence I.
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- Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source
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An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.
- Dogga, Bhushanarao,Joseph, Jayan T.,Kumar, C. S. Ananda
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supporting information
p. 309 - 313
(2020/12/23)
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- Solvent-free ruthenium-catalysed triflate coupling as a convenient method for selective azole-o-C-H monoarylation
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Metal-catalysed ortho-directed C-H functionalization usually faces selectivity issues in the competition between mono- and disubstitution processes. We report herein the ruthenium-catalysed N-directed C-H monoarylation of arylpyrazoles with a selectivity
- Abidi, Oumaima,Boubaker, Taoufik,Hierso, Jean-Cyrille,Roger, Julien
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supporting information
p. 5916 - 5919
(2019/06/24)
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- Directed ortho Metalation (D o M)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study
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A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (D o M) is reported. In general, the Suzuki-Miyaura and Negishi protocols show gre
- Quesnelle, Claude A.,Snieckus, Victor
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supporting information
p. 4395 - 4412
(2018/11/21)
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- Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron “Ate” Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger
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Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables “ate” complex formation and overcomes catalytic inhibition by halide ions.
- Lovinger, Gabriel J.,Aparece, Mark D.,Morken, James P.
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supporting information
p. 3153 - 3160
(2017/03/11)
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- A Nickel-Catalyzed Carbonyl-Heck Reaction
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The use of transition-metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni0 precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity- and reactivity-related challenges associated with more traditional Friedel–Crafts reactions. A Heck-type mechanism is postulated, wherein the π bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.
- Vandavasi, Jaya Kishore,Hua, XiYe,Halima, Hamdi Ben,Newman, Stephen G.
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supporting information
p. 15441 - 15445
(2017/11/10)
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- A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution
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The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid.
- Kassanova, Assiya Zh.,Krasnokutskaya, Elena A.,Beisembai, Perizat S.,Filimonov, Victor D.
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p. 256 - 262
(2016/01/15)
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- Nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds
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A nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds is disclosed. This reaction can proceed smoothly under a mild reaction condition, producing the corresponding aryl phosphorus compounds in good to high yields.
- Yang, Jia,Xiao, Jing,Chen, Tieqiao,Han, Li-Biao
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p. 120 - 124
(2016/08/23)
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- A new synthesis of pyridinyl trifluoromethanesulfonates via one-pot diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid
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The first method for the direct one-pot transformation of aminopyridines into pyridinyl trifluoromethanesulfonates is developed. The procedure involves diazotization of aminopyridines with sodium nitrite in a DMSO paste in the presence of trifluoromethanesulfonic acid.
- Krasnokutskaya, Elena A.,Kassanova, Assiya Zh.,Estaeva, Makpal T.,Filimonov, Victor D.
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supporting information
p. 3771 - 3773
(2014/07/07)
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- An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates
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The stable Pd(0) species [(1,5-cyclooctadiene)(L·Pd)2] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.
- Lee, Hong Geun,Milner, Phillip J.,Buchwald, Stephen L.
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supporting information
p. 5602 - 5605
(2013/11/19)
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- Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
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Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
- Seganish, W. Michael,DeShong, Philip
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p. 1137 - 1143
(2007/10/03)
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- Palladium-catalyzed phosphination of functionalized aryl triflates
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Catalytic user-friendly approach to the syntheses of various functionalized aromatic phosphines from their corresponding substituted aryl triflates and triarylphosphines was accomplished. This method is carried out in neutral media and compatible with man
- Kwong, Fuk Yee,Lai, Chi Wai,Yu, Michael,Tian, Yuan,Chan, Kin Shing
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p. 10295 - 10305
(2007/10/03)
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- CERTAIN (ARYLSULFONAMIDO- AND IMIDAZOLYL-)-SUBSTITUTED CARBOXYLIC ACIDS AND DERIVATIVES THEREOF AND USE FOR SUPPRESSING THROMBOXANE ACTIVITY
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The present invention is concerned with compounds of formula I STR1 wherein A, B, M, R, Ar and Het are as defined in the specification, pharmaceutically acceptable ester and amide derivatives thereof; N-oxides thereof, tetrazole derivatives thereof, and s
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- (Arylsulfonamido- and pyridyl-)-substituted carboxylic acids and derivatives thereof and use for suppressing thromboxane activity
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Disclosed are the compounds of formula STR1 wherein A represents lower alkylene; B represents oxygen, sulfur, lower alkylene, lower alkylene interrupted by oxygen, sulfur, sulfinyl or sulfonyl, (oxy-, sulfinyl-, sulfonyl- or thio)-lower alkylene, lower al
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