1996-41-4Relevant articles and documents
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Srivastava,K.C.
, p. 583 - 584 (1964)
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In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System
Nahide, Pradip D.,Ramadoss, Velayudham,Juárez-Ornelas, Kevin A.,Satkar, Yuvraj,Ortiz-Alvarado, Rafel,Cervera-Villanueva, Juan M. J.,Alonso-Castro, ángel J.,Zapata-Morales, Juan R.,Ramírez-Morales, Marco A.,Ruiz-Padilla, Alan J.,Deveze-álvarez, Martha A.,Solorio-Alvarado, César R.
, p. 485 - 493 (2018/02/09)
A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.
Multisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process
Arcadi, Antonio,Blesi, Federico,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Marinelli, Fabio
, p. 1857 - 1871 (2013/04/10)
Full details as well as the study of the scope, limitations, and further elaboration of a straightforward approach to the synthesis of 2,5,7-trisubstituted benzo[b]furans from 2-bromo- and 2-chloro-6-iodo-4- substituted phenols through a consecutive copper- and/or palladium-catalyzed assembly and functionalization process is described. Functionalization at the C(7) position is carried out by Suzuki-Miyaura cross-coupling, alkynylation, alkenylation, and C-N bond forming reactions. A one-pot protocol for the synthesis of 2,5,7-trisubstituted benzo[b]furans is also reported.