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Literature DB >> 25757054

An alternative to the Sandmeyer approach to aryl iodides.

Bao Hu¹, William H Miller, Kiel D Neumann, Ethan J Linstad, Stephen G DiMagno.

Abstract

Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

Entities: Chemical Gene

Keywords: Sandmeyer reaction; aryl iodides; diaryliodonium salt; electrophilic substitution; regioselectivity

Mesh：

Substances：

Year: 2015 PMID： 25757054 PMCID： PMC4412146 DOI： 10.1002/chem.201500151

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

7 in total

1. Mild silver(I)-mediated regioselective iodination and bromination of arylboronic acids.

Authors: Raed M Al-Zoubi; Dennis G Hall
Journal: Org Lett Date: 2010-06-04 Impact factor: 6.005

2. Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors.

Authors: Kushol Gupta; Carl J Kaub; Kristen N Carey; Eduard G Casillas; Barry S Selinsky; Patrick J Loll
Journal: Bioorg Med Chem Lett Date: 2004-02-09 Impact factor: 2.823

3. Mild arming and derivatization of natural products via an In(OTf)3-catalyzed arene iodination.

Authors: Cong-Ying Zhou; Jing Li; Satyamaheshwar Peddibhotla; Daniel Romo
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

4. N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics.

Authors: G K Surya Prakash; Thomas Mathew; Dushyanthi Hoole; Pierre M Esteves; Qi Wang; Golam Rasul; George A Olah
Journal: J Am Chem Soc Date: 2004-12-08 Impact factor: 15.419

5. Diaryliodonium salts: a journey from obscurity to fame.

Authors: Eleanor A Merritt; Berit Olofsson
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides.

Authors: Marcin Bielawski; Berit Olofsson
Journal: Chem Commun (Camb) Date: 2007-03-20 Impact factor: 6.222

7. N-IODOHYDANTOINS. II. IODINATIONS WITH 1,3-DIIODO-5,5-DIMETHYLHYDANTOIN.

Authors: O O ORAZI; R A CORRAL; H E BERTORELLO
Journal: J Org Chem Date: 1965-04 Impact factor: 4.354

7 in total

4 in total

An alternative to the Sandmeyer approach to aryl iodides.

1. Mild silver(I)-mediated regioselective iodination and bromination of arylboronic acids.

2. Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors.

3. Mild arming and derivatization of natural products via an In(OTf)3-catalyzed arene iodination.

4. N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics.

5. Diaryliodonium salts: a journey from obscurity to fame.

6. High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides.

7. N-IODOHYDANTOINS. II. IODINATIONS WITH 1,3-DIIODO-5,5-DIMETHYLHYDANTOIN.

1. Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts.

2. I(III)-Catalyzed Oxidative Cyclization-Migration Tandem Reactions of Unactivated Anilines.

3. A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

4. One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts.