122948-58-7

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 99-90-1 para-bromoacetophenone 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 13541-18-9 1-(4-bromophenyl)-3,3,3-trifluoropropan-1-one 
• 13541-19-0 3,3,3-trifluoro-1-(4-bromophenyl)-1-propanol 
• 4333-76-0 1-(4-bromophenyl)-1-phenylethene 
• 56913-50-9 1-(4-bromophenyl)-1-phenylethane 
• 122948-53-2 [2-(4-bromophenyl)prop-2-enyl]trimethylsilane 

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.

Urea-Catalyzed Vinyl Carbocation Formation Enables Mild Functionalization of Unactivated C-H Bonds

Herein we report the 3,5-bistrifluoromethylphenyl urea-catalyzed functionalization of unactivated C-H bonds. In this system, the urea catalyst mediates the formation of high-energy vinyl carbocations that undergo facile C-H insertion and Friedel-Crafts re

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

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

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.