1330681-27-0Relevant articles and documents
Refining boron-iodane exchange to access versatile arylation reagents
Karandikar, Shubhendu S.,Stuart, David R.
supporting information, p. 1211 - 1214 (2022/02/03)
Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components results in improved yield and faster reaction time compared to previous conditions. Mechanistic studies reveal a pathway that is more like transmetallation than SEAr.
Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts
Kervefors, Gabriella,Kersting, Leonard,Olofsson, Berit
, p. 5790 - 5795 (2021/03/08)
A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.
Catalyst-Free Arylation of Tertiary Phosphines with Diaryliodonium Salts Enabled by Visible Light
Bugaenko, Dmitry I.,Volkov, Alexey A.,Livantsov, Mikhail V.,Yurovskaya, Marina A.,Karchava, Alexander V.
supporting information, p. 12502 - 12506 (2019/09/16)
The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium salts an
N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines
Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
supporting information, p. 6389 - 6393 (2018/10/09)
Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.
A Modular Flow Design for the meta-Selective C?H Arylation of Anilines
Gemoets, Hannes P. L.,Laudadio, Gabriele,Verstraete, Kirsten,Hessel, Volker,No?l, Timothy
supporting information, p. 7161 - 7165 (2017/06/13)
Described herein is an effective and practical modular flow design for the meta-selective C?H arylation of anilines. The design consists of four continuous-flow modules (i.e., diaryliodonium salt synthesis, meta-selective C?H arylation, inline copper extraction, and aniline deprotection) which can be operated either individually or consecutively to provide direct access to meta-arylated anilines. With a total residence time of 1 hour, the desired product could be obtained in high yield and excellent purity without the need for column chromatography, and the residual copper content meets the standards for parenterally administered pharmaceutical substances.
Flow Synthesis of Diaryliodonium Triflates
Laudadio, Gabriele,Gemoets, Hannes P. L.,Hessel, Volker,No?l, Timothy
, p. 11735 - 11741 (2017/11/24)
A safe and scalable synthesis of diaryliodonium triflates was achieved using a practical continuous-flow design. A wide array of electron-rich to electron-deficient arenes could readily be transformed to their respective diaryliodonium salts on a gram scale, with residence times varying from 2 to 60 s (44 examples).
Cu-Mediated C-H 18F-Fluorination of Electron-Rich (Hetero)arenes
McCammant, Matthew S.,Thompson, Stephen,Brooks, Allen F.,Krska, Shane W.,Scott, Peter J. H.,Sanford, Melanie S.
, p. 3939 - 3942 (2017/07/26)
This communication describes a method for the nucleophilic radiofluorination of electron-rich arenes. The reaction involves the initial C(sp2)-H functionalization of an electron-rich arene with MesI(OH)OTs to form a (mesityl)(aryl)iodonium salt
Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts
Gonda, Zsombor,Novák, Zoltán
supporting information, p. 16801 - 16806 (2015/11/16)
A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.
Metal-free synthesis of ortho -CHO diaryl ethers by a three-component sequential coupling
Liu, Fangliang,Yang, Huameng,Hu, Xinquan,Jiang, Gaoxi
supporting information, p. 6408 - 6411 (2015/01/09)
A practical, metal-free, and highly chemoselective approach was developed for the synthesis of ortho-CHO diaryl ethers by a three-component sequential coupling of arynes, N,N-dimethylformamide (DMF), and diaryliodonium salts. Diverse functional groups including halo, nitryl, and bulky substituents and heteroaromatics are well tolerated. Mechanistically, isotopic tracer experiments reveal that the diaryliodonium salt serves as an electrophile to trap the transient intermediates generated from the [2 + 2] cyclization of an aryne and DMF.
Halogen exchange via a halogenation of diaryliodonium salts with cuprous halide
Li, Jian,Liu, Li,Ding, Dong,Sun, Jiang-Tao
, p. 541 - 548 (2014/01/06)
An efficient halogenation reaction has been developed with diaryliodonium salts and cuprous halides. Various diaryliodonium salts 1 could perform the reaction with readily available CuBr or CuCl in CH3CN at 80°C, assembling bromoarenes or chloroarenes in up to 92% yields. This provides us a method for the transformation from iodoarenes to other haloarenes.
