2012-29-5Relevant articles and documents
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Vortmann
, p. 236 (1923)
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ON THE PRODUCT DISTRIBUTION IN THE IODINATION OF PHENOL
Rossi, Rita H. de,Veglia, Alicia V.
, p. 5963 - 5966 (1986)
The product distribution in the iodination of phenol with I2 in water solution is buffer and pH dependent with the ortho product increasing at low pH and low buffer concentration.This effect is attributed to different rates of proton transfer form the 4-iodo-2,5-; and 2-iodo-3,5-cyclohexadienone intermediate.
Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
, p. 4149 - 4164 (2019/04/30)
An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation
Ikoma, Atsushi,Ogawa, Narihito,Kondo, Daiki,Kawada, Hiroki,Kobayashi, Yuichi
supporting information, p. 2074 - 2077 (2016/06/01)
A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (-)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed coupling with allylborate. The aforementioned iodide was synthesized using a new method for ortho-selective deiodination of o-,p-diiodophenols.