Preparation of aryl chlorides from phenols

Bay, Elliott; Bak, David A.; Timony, Peter E.; Leone-Bay, Andrea

doi:10.1021/jo00297a087

Cited by 22 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Considering the remarkable advantages of aryl triflates toward sustainable chemical synthesis, simple and efficient protocols that can transform aryl triflates into aryl iodides would be desirable. To achieve this goal, harsh conditions , or multistep syntheses , were usually required. However, a few relatively general metal-catalyzed methods have recently been disclosed.…”

Section: Results and Discussionmentioning

confidence: 99%

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

et al. 2017

View full text Add to dashboard Cite

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Simple aryl halides are conventionally prepared by electrophilic aromatic substitution with halogens or the Sandmeyer reaction under relatively harsh conditions. For the synthesis of relatively complicated ones, a three-step scheme starting from phenols and consisting of trifluoromethanesulfonylation, palladium-catalyzed stannylation/borylation, and halogenolysis has been widely used as a reliable method. − As a straightforward method, Buchwald and co-workers have recently developed a palladium-catalyzed direct transformation of aryl and alkenyl triflates to the corresponding bromides and chlorides . However, it is not applicable to the synthesis of aryl iodides.…”

mentioning

confidence: 99%

Ruthenium-Catalyzed Transformation of Aryl and Alkenyl Triflates to Halides

et al. 2012

View full text Add to dashboard Cite

Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)(3)]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η(1)-arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.

show abstract

“…Converting phenol 5 into aryl halides, which can undergo cross-coupling with active methylene compounds such as malononitrile in the presence of Pd catalysts, is thereby highly desirable. Few methods have been reported for direct conversion of phenols to aryl halides . Attempts to synthesize 6b via thermolysis of the phenol-triphenylphosphine dibromide complex 19a were unsuccessful.…”

mentioning

confidence: 99%

Efficient Synthesis and Structural Characteristics of Zwitterionic Twisted π-Electron System Biaryls

Kang¹,

Facchetti²,

Stern³

et al. 2005

Org. Lett.

View full text Add to dashboard Cite

A series of unconventional twisted pi-electron system molecules has been synthesized via Suzuki cross-coupling of two sterically hindered arenes. Crystallographic analysis of these molecules reveals a large ring-ring dihedral twist angle (87 degrees ) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported. [reaction: see text]

show abstract

Preparation of aryl chlorides from phenols

Cited by 22 publications

References 0 publications

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Ruthenium-Catalyzed Transformation of Aryl and Alkenyl Triflates to Halides

Efficient Synthesis and Structural Characteristics of Zwitterionic Twisted π-Electron System Biaryls

Contact Info

Product

Resources

About