- Straightforward Access to Thiocyanates via Dealkylative Cyanation of Sulfoxides
-
Thiocyanates, versatile building blocks in organic synthesis, are shown to be easily accessible via an interrupted Pummerer reaction of sulfoxides. This facile dealkylative functionalization proceeds under mild conditions through electrophilic activation of the sulfoxide partner. The resulting thiocyanate itself can serve as a handle for diversification in a straightforward one-pot procedure.
- Todorovi?, Uro?,Klose, Immo,Maulide, Nuno
-
supporting information
p. 2510 - 2513
(2021/04/13)
-
- Synthesis of Alkyl Silanes via Reaction of Unactivated Alkyl Chlorides and Triflates with Silyl Lithium Reagents
-
The reaction of unactivated secondary and primary alkyl chlorides as well as primary alkyl triflates with silyl lithium reagents to access tetraorganosilanes is reported. These nucleophilic substitutions proceed in the absence of any transition metal catalyst under mild conditions in moderate to very good yields. The silyl lithium reagents are readily generated from the corresponding commercially available chlorosilanes. Enantioenriched secondary alkyl chlorides react with high stereospecificity under inversion of configuration.
- Mallick, Shubhadip,Würthwein, Ernst-Ulrich,Studer, Armido
-
supporting information
p. 6568 - 6572
(2020/09/02)
-
- Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
-
Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).
- Liu, Shiwen,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
-
supporting information
p. 3667 - 3671
(2018/09/12)
-
- CATALYST AND PROCESS FOR SYNTHESISING THE SAME
-
The invention relates to a method for synthesising tethered ruthenium catalysts and novel tethered ruthenium catalysts obtainable by this methods. The method involves carrying out an "arene swapping" reaction avoiding the requirement to use complicated techniques making use of unreliable Birch reductions and unstable cyclodienyl intermediates.
- -
-
Page/Page column 17; 18
(2014/05/24)
-
- Mild copper-catalyzed fluorination of alkyl triflates with potassium fluoride
-
A chemoselective catalytic fluorination of alkyl triflates is described using potassium fluoride as a fluoride source. Excellent yields of the desired alkyl fluorides are obtained after one hour at 45°C using 2 mol% of the copper catalyst. With 10 mol% of the catalyst, full conversion can be achieved in less than 10 minutes at 45°C, and thus makes this procedure potentially suited for the preparation of 18F-labeled PET probes. As a result of the mild reaction conditions, only the substitution products are observed with no evidence of common side reactions, such as elimination. Reported is a preliminary study of the reaction scope, which demonstrates that the fluorination can be performed in the presence of a wide range of functional groups. Evidence suggests an unusual role of the [IPrCuOTf] catalyst as a phase-transfer catalyst and points to [IPrCuF] as the active fluorinating reagent (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).
- Dang, Hester,Mailig, Melrose,Lalic, Gojko
-
supporting information
p. 6473 - 6476
(2014/06/24)
-
- Synthesis of azide-alkyne fragments for 'click' chemical applications. formation of chiral 1,4-disubstituted-(β-alkyl) γ- 1,2,3-triazole scaffolds from orthogonally protected chiral β-alkyl-trialkylsilyl γ- Pentynyl azides and chiral β-alkyl γ- Pentynyl-alcohols
-
A library of chiral γ-pentynyl alcohols and γ-pentynyl azides was made using the SuperQuat auxiliary. Coupling of the free alkynes with the azides by Huisgen 1,3-dipolar cycloaddition provided chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as possible peptidomimetic compounds.
- Montagnat, Oliver D.,Lessene, Guillaume,Hughes, Andrew B.
-
scheme or table
p. 1541 - 1549
(2011/09/16)
-
- A Simple Preparation of Alkyl Trifluoromethanesulfonates (Triflates) from Alkyl Trimethylsilyl Ethers
-
Several alkyl trifluoromethanesulfonates (triflates) 2 are prepared by reacting alkyl trimethylsilyl ethers 1 with trifluoromethanesulfonic anhydride.The triflates 2 can be used for further reactions without isolation, as illustrated in the preparation of the ether 3 and cumene (4).
- Aubert, Corinne,Begue, Jean-Pierre
-
p. 759 - 760
(2007/10/02)
-