120976-84-3Relevant academic research and scientific papers
High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides
Bielawski, Marcin,Olofsson, Berit
, p. 2521 - 2523 (2007)
Unsymmetric and symmetric diaryliodonium triflates are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol employing arenes and aryl iodides or iodine. The Royal Society of Chem
Practical synthesis of diaryliodonium(iii) triflates using ArI(OAc)2/TfOH/MeCN reaction system
Dohi, T.,Kikushima, K.,Kita, Y.,Kobayashi, S.,Komiyama, K.,Shoji, T.
, p. 2328 - 2332 (2020/12/31)
Diaryliodonium(iii) triflates were synthesized in a safe manner by the reaction of aryliodine(iii) diacetates ArI(OAc)2 with triflic acid (TfOH) in MeCN under mild exothermic conditions. This method provides access to a variety of diaryliodoniu
Arylation with unsymmetrical diaryliodonium salts: A chemoselectivity study
Malmgren, Joel,Santoro, Stefano,Jalalian, Nazli,Himo, Fahmi,Olofsson, Berit
supporting information, p. 10334 - 10342 (2013/09/02)
Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents. Copyright
Synthesis of diaryliodonium triflates using environmentally benign oxidizing agents
Merritt, Eleanor A.,Malmgren, Joel,Klinke, Felix J.,Olofsson, Berit
experimental part, p. 2277 - 2280 (2009/12/08)
A range of symmetric and unsymmetric diaryliodonium triflates have been prepared employing urea-hydrogen peroxide as the oxidizing agent. The use of aqueous hydrogen peroxide and catalytic systems with methylrhenium trioxide in the oxidation of iodoarenes
Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations
Bielawski, Marcin,Zhu, Mingzhao,Olofsson, Berit
, p. 2610 - 2618 (2008/09/19)
Symmetrical and unsymmetrical diaryliodonium triflates have been synthesized from both electron-deficient and electron-rich arenes and aryl iodides with mCPBA and triflic acid. A thorough investigation of the optimization, scope and limitations has resulted in an improved one-pot protocol that is fast, high-yielding, and operationally simple. The reaction has been extended to the direct synthesis of symmetrical iodonium salts from iodine and arenes, conveniently circumventing the need for aryl iodides.
An efficient ligand exchange reaction of (e)-[β- (trifluoromethanesulfonyloxy)ethenyl](phenyl)iodonium triflates with aryl- and alkynyllithium reagents leading to diaryl- and alkynyliodonium triflates
Pirguliyev, Namig Sh,Brel, Valery K.,Akhmedov, Navruz G.,Zefirov, Nikolai S.
, p. 81 - 83 (2007/10/03)
Reaction of (E)-[β-(trifluoromethanesulfonyloxy)- ethenyl](phenyl)iodonium triflates with aryl- and alkynyllithium reagents gave aryl(phenyl)- and alkynyl(phenyl)iodonium triflates in high yields and selectively. These reactions indicate that ligand exchange takes place efficiently at the hypervalent iodine atom and provides another approach to diaryl- and alkynyliodonium salts.
A convenient preparation of diaryliodonium triflates
Kitamura,Matsuyuki,Nagata,Furuki,Taniguchi
, p. 945 - 946 (2007/10/02)
A reagent prepared from iodosylbenzene and trifluoromethanesulfonic acid reacts with aromatic compounds to give diaryliodonium triflates in good yields. A high reactivity of the reagent is also discussed.
