Copper‐Catalyzed Asymmetric Ring‐Opening of Cyclic Diaryliodonium with Benzylic and Aliphatic Amines

Xu, Shibo; Zhao, Kun; Gu, Zhenhua

doi:10.1002/adsc.201800637

Cited by 57 publications

(26 citation statements)

References 57 publications

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“…The phenomenon may be ascribed to the fact that electron-poor aryl groups are transferred more readily than electron-rich aryl groups in the arylation reaction of unsymmetric diaryliodonium saltsw ith P(O)-OH compounds. [10] To our surprise, when 6-H-6'-methoxy-[1,1'-biphenyl]-2,2'-iodonium triflate (1l)w as used for the reaction, there is only 2'-iodo-6'-methoxy-[1,1'-biphenyl]-2-yl diphenylphosphinate (4k)g enerated in 67 %y ield after the reaction. However,amixturew as obtained when 4-H-4'-acetyl-[1,1'-biphenyl]-2,2'-iodonium triflate( 1m)w as adopted as the couplingp artner for the reaction.…”

Section: Resultsmentioning

confidence: 96%

“…The collected solid was washed with Et 2 O three times, dried in vacuo to afford 1 a (1.68 g, 98 % yield) as a white powder. Compounds of 1 b – m were synthesized by the general procedure A , B , C. 1 a (yield: 81 %), 1 b (yield: 75 %), 1 c (yield: 69 %), 1 d (yield: 43 %), 1 e (yield: 65 %), 1 f (yield: 46 %), 1 g ((yield: 60 %), 1 i ((yield: 71 %), 1 j ((yield: 68 %), 1 l ((yield: 36 %), 1 m ((yield: 77 %), 1 h (yield: 29 %) and 1 k (yield: 55 %) are new compounds.…”

Section: Methodsmentioning

confidence: 99%

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Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

Wang

Xiong

Zhou

et al. 2019

Chemistry An Asian Journal

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Section: Resultsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

Wang

Xiong

Zhou

et al. 2019

Chemistry An Asian Journal

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“… 467 Further mechanistic insights, and an improved experimental procedure, in which the amine is added slowly via a syringe pump, leading to an expanded substrate scope (benzylic and aliphatic amines) were subsequently reported by Gu. 468 …”

Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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“…Further, Cu(III)‐intermediate coordinates with benzylamine followed by deprotonation. Deprotonated complex undergo reductive elimination to give final product with regeneration of catalyst [55] …”

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

confidence: 99%

“…Deprotonated complex undergo reductive elimination to give final product with regeneration of catalyst. [55]…”

Section: Ring-opening Of Cyclic Diaryliodonium Saltsmentioning

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 Asymmetric Ring‐Opening of Cyclic Diaryliodonium with Benzylic and Aliphatic Amines

Cited by 57 publications

References 57 publications

Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

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

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