Copper-Catalyzed Enantioselective Ring-Opening of Cyclic Diaryliodoniums and <i>O</i>-Alkylhydroxylamines

Li, Qigang; Zhang, Mingkai; Zhan, Shuming; Gu, Zhenhua

doi:10.1021/acs.orglett.9b02267

Cited by 52 publications

(24 citation statements)

References 52 publications

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“…The newly obtained results indicated that these cMAVIs were vulnerable to triethylamine. On the other hand, their instability to bases implied that they might be highly reactive even without a transition metal, which is unusual for traditional cDAIs ( Li et al., 2019 ; Wu and Yoshikai, 2015 ). It would be valuable if their reactivity could be tuned under refined conditions.…”

Section: Resultsmentioning

confidence: 99%

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

et al. 2020

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Summary Cross-coupling reactions between aryl iodide and nucleophiles have been well developed. Iodoniums equipped with a reactive C-I(III) bond accelerate cross-coupling reactions of aryl iodide. Among them, cyclic diaryliodoniums are more atom economical; however; they are often in the trap of metal reliance and encounter regioselectivity issues. Now, we have developed a series of highly reactive cyclic monoaryl-vinyl iodoniums that can be tuned to construct C-N, C-O, and C-C bonds without metal catalysis. Under promotion of triethylamine, coupling reactions with aniline, phenol, aromatic acid, and indole proceed rapidly and regioselectively at room temperature. The carbene species is conceptualized as a key intermediate in our mechanism model. Furthermore, the coupling products enable diversity-oriented synthesis strategy to further build up a chemical library of diverse heterocyclic fragments that are in demand in the drug discovery field. Our current work provides a deep insight into the synthetic application of these highly reactive cyclic iodoniums.

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Section: Resultsmentioning

confidence: 99%

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

et al. 2020

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“…In this case, a different Cu I /BOX (BOX = bisoxazoline) complex was used as the catalyst. 22 Aiming to introduce new functionalities into this system, the same group reported a Cu-catalysed asymmetric thiolative ring opening reaction for the synthesis of atropisomeric 2-thio-2 0 -iodo-1,1 0 -biphenyl derivatives. 23 In this case, the use of potassium thiocarboxylates as nucleophiles and Cu(CH 3 CN) 4 PF 6 /PhBOX as the optimal catalytic system delivered the desired thioesters satisfactorily in terms of reactivity and enantioselectivity (Scheme 10D).…”

Section: Desymmetrization Of Biaryls Via Ring-opening Reactions ‡mentioning

confidence: 99%

Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies

et al. 2021

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“…reported copper‐catalyzed enantioselective ring‐opening of cyclic diaryliodoniums and O ‐alkylhydroxylamines (Scheme 41). The base CaO played an important role in preventing side reactions and reaction gave high yields and the ligand 3,5‐di( t butyl)phenyl bis(oxazoline) gave high stereoselectivity [50] …”

Section: Transformations Involving Hypervalent Iodine Reagents and 1s...mentioning

confidence: 99%

“…The base CaO played an important role in preventing side reactions and reaction gave high yields and the ligand 3,5-di( t butyl)phenyl bis(oxazoline) gave high stereoselectivity. [50] Scheme 39. Aminotrifluoromethylation of alkenes.…”

Section: Ring-opening Of Cyclic Diaryliodonium Salts and O-hydroxylam...mentioning

confidence: 99%

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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Copper-Catalyzed Enantioselective Ring-Opening of Cyclic Diaryliodoniums and O-Alkylhydroxylamines

Cited by 52 publications

References 52 publications

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions

Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies

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

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