Unknown

Dataset Information

0

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides.

ABSTRACT: A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

SUBMITTER: Leas DA 

PROVIDER: S-EPMC5572204 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides.

Leas Derek A DA   Dong Yuxiang Y   Vennerstrom Jonathan L JL   Stack Douglas E DE  

Organic letters 20170508 10

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a S<sub>RN</sub>1 mechanism. This method represen  ...[more]

Similar Datasets

Unknown Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides.
| S-EPMC6008600 | biostudies-literature
Unknown One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.
| S-EPMC5369543 | biostudies-literature
Unknown Metal-Free Radical Borylation of Alkyl and Aryl Iodides.
| S-EPMC6470957 | biostudies-literature
Unknown HCl•DMPU-Assisted One-pot and Metal-free Conversion of Aldehydes to Nitriles.
| S-EPMC8009297 | biostudies-literature
Unknown Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone.
| S-EPMC5288754 | biostudies-literature
Unknown One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid.
| S-EPMC5905280 | biostudies-literature
Unknown Metal-Free Synthesis of Aryltriphenylphosphonium Bromides by the Reaction of Triphenylphosphine with Aryl Bromides in Refluxing Phenol.
| S-EPMC6648432 | biostudies-literature
Unknown Copper/N,N-dimethylglycine catalyzed goldberg reactions between aryl bromides and amides, aryl iodides and secondary acyclic amides.
| S-EPMC6271110 | biostudies-literature
Unknown The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.
| S-EPMC4134717 | biostudies-literature
Unknown Chemical Conversion of Hardly Ionizable Rhenium Aryl Chlorocomplexes with p-Substituted Anilines.
| S-EPMC8201000 | biostudies-literature