Rhenium‐Catalyzed Decarboxylative Tri‐/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid‐Derived Hypervalent Iodine Reagents

Wang, Yin; Yang, Yaxi; Wang, Congyang

doi:10.1002/cjoc.201900296

Cited by 24 publications

(9 citation statements)

References 99 publications

(13 reference statements)

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“…Furthermore, in 2019, Gouverneur reported the hydrodifluoromethylation of alkenes by an in situ‐ generated [bis(difluoroacetoxy)iodo]benzene [11] . Wang and coworkers reported a decarboxylative difluoromethylation of styrenes with [bis(difluoroacetoxy)iodo]benzene by rhenium catalysis [12] . However, the difluoromethylation of alkynes by this novel difluoromethyl radical precursor has yet to be reported.…”

Section: Methodsmentioning

confidence: 99%

“…[11] Wang and coworkers reported a decarboxylative difluoromethylation of styrenes with [bis(difluoroacetoxy)iodo]benzene by rhenium catalysis. [12] However, the difluoromethylation of alkynes by this novel difluoromethyl radical precursor has yet to be reported. Thus, we herein describe the catalyst-free direct difluoromethylation of alkynoates by [bis(difluoroacetoxy)iodo]benzene for the synthesis of 3-difluoromethylated coumarins (Scheme 1).…”

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confidence: 99%

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Visible‐Light‐Induced Radical Difluoromethylation of Alkynoates by [bis(Difluoroacetoxy)iodo]benzene to Yield 3‐Difluoromethylated Coumarins

Zhou

Jia

et al. 2021

Asian J Org Chem

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A visible‐light‐induced radical difluoromethylation of alkynoates using [bis(difluoroacetoxy)iodo]benzene as the CF2H radical precursor was developed for the first time. 3‐Difluoromethyl‐substituted coumarins were synthesized via a radical difluoromethylation/cyclization/ester migration cascade. The mild and catalyst‐free conditions, as well as the good functional group tolerance, render this protocol an alternative and green strategy for the synthesis of 3‐difluoromethyl‐substituted coumarins.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Visible‐Light‐Induced Radical Difluoromethylation of Alkynoates by [bis(Difluoroacetoxy)iodo]benzene to Yield 3‐Difluoromethylated Coumarins

Zhou

Jia

et al. 2021

Asian J Org Chem

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“…Different phosphorous‐substituted olefins were also functionalized to form α ‐oxygenated β ‐trifluoromethylated phosphates. The reaction scope was expanded by using different halogen‐substituted hypervalent iodine reagents [114] …”

Section: Transformations Involving Hypervalent Iodine Reagents and 3r...mentioning

confidence: 99%

“…The process was well tolerated with 1° and 2° α , β ‐unsaturated esters and amides. The substrate scope was broaden up by different halogens and source of halogens substituted to aryl rings [114] …”

Section: Transformations Involving Hypervalent Iodine Reagents and 3r...mentioning

confidence: 99%

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Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

et al. 2022

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This review outlines the progress over recent years in the reactions involving combined approach of hypervalent iodine reagents and transition metals such as palladium, nickel, iridium, gold, rhodium, copper, iron, ruthenium, platinum, silver, zinc, rhenium and cobalt. This approach enables organic transformations complimentary to traditional manifolds. Hypervalent iodine reagents play a preeminent role in organic chemistry due to their versatile reactivity, heteroatom ligands and mild reaction conditions. These reagents in combination of transition metal compounds are used in many synthetically useful organic reactions such as oxidation, rearrangement, amination, halogenation, amidation, ring-opening, cyclization and CÀ H and CÀ C functionalization reactions, etc. which are discussed here. Combination with Cobalt 2.3. Reactions of Hypervalent Iodine Reagents with Copper 2.4. Reactions of Hypervalent Iodine Reagents in Combination with Nickel 2.5. Reactions of Hypervalent Iodine Reagents in Combination with Zinc 3. Transformations Involving Hypervalent Iodine Reagents and 2 nd Transition Series Metals 3.1. Reactions of Hypervalent Iodine Reagents in Combination with Ruthenium 3.2. Reactions of Hypervalent Iodine Reagents in Combination With Rhodium 3.3. Reactions of Hypervalent Iodine Reagent in Combination With Palladium 3.4. Reactions of Hypervalent Iodine Reagents in Combination with Silver 4. Transformations Involving Hypervalent Iodine Reagents and 3rd Transition Series Metals 4.1. Reactions of Hypervalent Iodine Reagents in Combination with Rhenium 4.2. Reactions of Hypervalent Iodine Reagents in Combination with Iridium 4.3. Reactions of Hypervalent Iodine Reagents in Combination with Platinum 4.4. Reactions of Hypervalent Iodine Reagents in Combination with Gold 5. Conclusion

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Visible‐Light Induced Ipso‐Difluoromethylation of N‐Arylpropiolamides to Synthesize 3‐Difluoromethyl Spiro[4.5]trienones

et al. 2022

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A visible light-induced radical ipso-difluoromethylation of N-arylpropiolamides to synthesize 3-difluoromethyl spiro[4.5]trienones was developed for the first time. In this transformation PhI(O 2 CCHF 2 ) 2 was used as difluoromethylation reagent and PhI(OAc) 2 was employed as oxidant. Due to the cheap and readily accessible reagents and oxidant as well as the mild reaction conditions, this method is as an efficient and practical strategy for the synthesis of difluoromethyl-substituted spiro[4.5]trienones.

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Rhenium‐Catalyzed Decarboxylative Tri‐/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid‐Derived Hypervalent Iodine Reagents

Cited by 24 publications

References 99 publications

Visible‐Light‐Induced Radical Difluoromethylation of Alkynoates by [bis(Difluoroacetoxy)iodo]benzene to Yield 3‐Difluoromethylated Coumarins

Visible‐Light‐Induced Radical Difluoromethylation of Alkynoates by [bis(Difluoroacetoxy)iodo]benzene to Yield 3‐Difluoromethylated Coumarins

Combined Approach of Hypervalent Iodine Reagents and Transition Metals in Organic Reactions

Visible‐Light Induced Ipso‐Difluoromethylation of N‐Arylpropiolamides to Synthesize 3‐Difluoromethyl Spiro[4.5]trienones

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