Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane

Hokamp, Tobias; Dewanji, Abhishek; Lübbesmeyer, Maximilian; Mück‐Lichtenfeld, Christian; Würthwein, Ernst‐Ulrich; Studer, Armido

doi:10.1002/anie.201706534

Cited by 57 publications

(28 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Aryl chlorides and aryl fluorides have been challenging substrates in the hydrodehalogenative reactions. To date, few successful examples have been reported . We were delighted to find that with aryl chlorides or fluorides used as the reaction substrates, this hydrodechlorination process occurred smoothly under the current optimized reaction conditions (Table ).…”

Section: Figurementioning

confidence: 99%

Hydrodehalogenation of Aryl Halides through Direct Electrolysis

Wang

Zhou

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

A catalyst‐ and metal‐free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu3N/Et3N behave as effective reductants and hydrogen atom donors for this electrochemical reductive reaction. Various aryl and heteroaryl bromides worked effectively. The typically less reactive aryl chlorides and fluorides can also be smoothly converted. The utility of our method is demonstrated by detoxification of harmful pesticides and hydrodebromination of a dibrominated biphenyl (analogues of flame‐retardants) in gram scale.

show abstract

Section: Figurementioning

confidence: 99%

Hydrodehalogenation of Aryl Halides through Direct Electrolysis

Wang

Zhou

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…[24] Alternatively,t he reaction could proceed by insertion of the olefin into aR u ÀCb ond, however this insertion would be expected to be slow. [25] Our proposed radical mechanism [26,27] [23] this intermediate can also re-enter the main cycle by the reaction with iPrO À .…”

Section: Zuschriftenmentioning

confidence: 90%

Catalytic Reduction of Alkyl and Aryl Bromides Using Propan‐2‐ol

2017

View full text Add to dashboard Cite

Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan‐2‐ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin‐based conditions for these reductions.

show abstract

“… 11 The activation of the C–Cl bond in unactivated chloroarenes is still rather challenging. 12 This is due to the stepwise C–Br/C–Cl bond activation process with a slow C–X cleavage step, 13 as well as the increasing difficulty for bromo-/chloroarene activation with respect to both reduction potential 14 and bond strength 15 ( Scheme 1b ). Herein, we report the discovery of a highly active promoter, indoline, based on the structural modification of existing promoters for carbon–halogen bond activation.…”

Section: Introductionmentioning

confidence: 99%