28143-79-5

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 98-86-2 acetophenone 
• 1493-13-6 trifluorormethanesulfonic acid 
• 536-74-3 phenylacetylene 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 29788-12-3 1-phenylethenyl fluorosulfonate 
• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 54010-75-2 zinc trifluoromethanesulfonate 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 2206-26-0 [D₃]acetonitrile 

Downstream Products

• 62676-19-1 2,4-diphenylbut-1-en-3-yne 
• 118716-35-1 2-butoxy-3-phenyl-1,3-butadiene 
• 530-48-3 1,1-Diphenylethylene 
• 51246-20-9 1-phenyl-1-iodoethylene 
• 1666-86-0 2,4,6-triphenylpyrimidine 
• 64571-30-8 2,4-dimethyl-6-phenylpyrimidine 
• 86984-23-8 2,6-diethyl-4-phenylpyrimidine 
• 98-81-7 1-bromovinylbenzene 
• 62698-27-5 α-phenylvinyl cation 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 1166996-31-1 2-(1,4-dioxan-2-yl)-1-phenylethan-1-one 
• 6938-44-9 ethyl 2-methyl-4-oxo-4-phenyl-butanoate 
• 23033-65-0 2-cyclopentyl-1-phenylethan-1-one 
• 5653-09-8 2-cyclohexyl-1-phenylethan-1-one 

Relevant academic research and scientific papers

A base-controlled switch of SO2 reincorporation in photocatalyzed radical difunctionalization of alkenes

Control of selectivity is a pivotal challenge in radical chemistry owing to the high reactivity and instability of radical species. Herein, a switchable, base-controlled strategy toward the reincorporation/release of SO2 in photocatalyzed radical difunctionalization of alkenes has been described. By this chemodivergent strategy, a variety of valuable, otherwise difficult-to-access γ-trifluoromethylated ketones and trifluoromethylated sulfonyl ketones can be selectively furnished from the same starting materials. This method features high chemoselectivity, a broad substrate scope, excellent functional group tolerance, and facile scale-up and was applied in a one-pot synthetic procedure. Evaluation of the reaction conditions and mechanistic studies indicate that the choice of base can invert the chemoselectivity of the reaction, demonstrating control over a challenging radical selectivity pattern.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation

Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α-arylated and α-oxyamina

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3

1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination of TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only terminal alkynes were selectively

Structural elucidation of supported Rh complexes derived from RhCl(PPh3)3 immobilized on surface-functionalized SBA-15 and their catalytic performance for C-heteroatom (S, O) bond formation

The local structures of rhodium complexes derived from the immobilization of Wilkinson's complex, RhCl(PPh3)3, on SBA-15 silica functionalized with primary–amine, secondary–amine, or diphenylphosphine groups within the mesoporous channels were characterized by a series of techniques including XRD, HR-TEM, multinuclear (13C/29Si/31P) solid-state NMR, 2D 31P{1H} HETCOR NMR, XPS, and Rh K-edge EXAFS. Immobilization of RhCl(PPh3)3 through covalent bond formation with different functional groups grafted to the silica surface lead to variations in the local structure of the Rh center that has important implications for catalysis. The immobilized Rh complexes demonstrated high activity for the addition of alkynes with thiols (hydrothiolation) or sulfonic acids (hydrosulfonation) with excellent regio- and stereoselectivity under mild reaction conditions. This work demonstrates the elucidation of the local structure of the immobilized Rh complexes requires a complimentary multi-technique characterization approach that probes both the metal center itself and surrounding ligands.

Visible light induced Trifluoromethyl Migration: Easy Access to α-Trifluoromethylated Ketones from Enol Triflates

Herein, we reported a novel method to synthesize α-trifluoromethylated ketones from enol triflates. Involving a cascade sulfur dioxide extrusion and a CF3 (trifluoromethyl) radical addition process, this reaction proceeds at room temperature an

Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones

We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

Zinc(II) catalyzed conversion of alkynes to vinyl triflates in the presence of silyl triflates

The conversion of alkynes to their corresponding vinyl triflates in the presence of stoichiometric TMS-triflate was greatly facilitated by the triflate salt of several transition metal catalysts most especially Zn(OTf)2. Products are formed in high regioselectivity under mild conditions. Internal alkynes bearing an aryl substituent afford vinyl triflates with a modest preference for the Z-isomer especially with larger substituents. A mechanism is put forward to explain the unique role of silicon in this system.