Direct Lactone Formation by Using Hypervalent Iodine(III) Reagents with KBr via Selective C−H Abstraction Protocol

Dohi, Toshifumi; Takenaga, Naoko; Goto, Akihiro; Maruyama, and Akinobu; Kita, Yasuyuki

doi:10.1021/ol071315n

Cited by 119 publications

(55 citation statements)

References 27 publications

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“…7‐Phenyloxepan‐2‐one (33c): 31,32 The bpa precursor 33b was transformed into the pertinent lactone 33c according to General Procedure E. Evaporation of the solvent led to lactone 33c (27.3 mg, 0.14 mmol, 79 %) as a white solid, m.p. 68 °C.…”

Section: Methodsmentioning

confidence: 99%

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

2014

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We describe a general and versatile approach for the conversion of carboxylic acid amides into their corresponding esters despite the fact that the former are thermodynamically more stable. The transformations are mediated by the coordination of CuI by a chelating entity. The resulting weakening of the amide bond allows for nucleophilic attack by alcoholic hydroxyl functions. The principle is demonstrated for a wide variety of transformations, leading to different kinds of esters and lactones.

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Section: Methodsmentioning

confidence: 99%

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

2014

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“…Numerous methods for the preparation and modification of halogenolactones have been reported in the literature . In our previous work, we presented the synthesis pathways and cytotoxic properties of iodine and hydroxylactones against the tumor cell lines HL‐60, U‐2 OS and D ‐17 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans‐γ‐Halo‐δ‐lactones

et al. 2018

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A new four‐step pathway for the synthesis of γ‐halo‐δ‐lactones is described from simple, commercially available substrates: aryl bromides and 3‐methyl crotonaldehyde. The halogenolactonization reaction of β,δ‐substituted, γ,δ‐unsaturated carboxylic acid 4 a–c is regio‐ and stereoselective and gives only the trans‐isomers of lactones 5 a–c, 6 a–c, and 7 a–c. The structures of all synthesized compounds were confirmed by using spectroscopic methods. For bromolactone, containing a naphthyl moiety in the structure, crystallographic analysis was also performed. The lactones were tested for their cytotoxic activity against L929 cell lines (mouse fibroblasts) and antibacterial activity against Escherichia coli strains ATCC 8739 and Staphylococcus aureus ATCC 65389. Compounds 5 a, 5 c, 7 a, and 7 b statistically significantly inhibited the metabolic activity of mouse fibroblasts L929. Compounds 5 b and 6 a were not cytotoxic towards L929 cells, but showed moderate bactericidal properties.

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“…We have therefore continuously studied the development of a direct functionalization method of carbonhydrogen bonds with hypervalent iodine reagents and developed new basic reactions utilizing the unknown active species derived from the iodine(III) reagents during this study. [50][51][52][53][54][55][56][57][58] They are promising as a new environmentally benign synthetic methods for replacing reactions using rare metals. As iodine is one of the few elements in which Japan is self-sufficient, producing about 40% of the total world supply, and most iodine derivatives show lower long-term toxicities compared with metal elements, the establishment of new synthetic methods enabling the practical use of iodines would have a significant benefit for Japan with its poor endowment of natural resources.…”

Section: Discussionmentioning

confidence: 99%

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

Dohi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxidation reactions consist of a number of important transformations in organic synthesis. However, in spite of their utility in both laboratory-and industrial-scale production, oxidations are among the most problematic processes regarding the factors of safety, environmental friendliness, operational simplicity, etc. As oxidants, hypervalent iodines, such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA), are among promising reagents for developing environmentally benign oxidation reactions due to their low toxicities, mild reactivity, ready availability, high stability, and easy handling. Our research objective is, largely in consideration of economic and environmental viewpoints, to enhance the synthetic values of these reagents as useful alternatives to highly toxic heavy-metal oxidants and even rare transition metals by pioneering their efficient utilization methods and unique reactivities. During this study, we have succeeded in the development of new recyclable reagents 1 and their catalytic utilization, and the design of a new chiral reagent 2 and its application to perform asymmetric oxidations. Accordingly, the recycling and catalytic use of a hypervalent iodine reagent became possible in many representative types of oxidative bond-forming reactions, some of which even include key transformations for natural product synthesis. A summary of these important achievements in hypervalent iodine chemistry are described in this review.

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Direct Lactone Formation by Using Hypervalent Iodine(III) Reagents with KBr via Selective C−H Abstraction Protocol

Abstract: We have developed a new and reliable method for the direct construction of biologically important aryl lactones and phthalides from carboxylic and benzoic acids, using a combination of hypervalent iodine(III) reagents with KBr.

Cited by 119 publications

References 27 publications

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans‐γ‐Halo‐δ‐lactones

Recycling and Catalytic Approaches for the Development of a Rare-Metal-Free Synthetic Method Using Hypervalent Iodine Reagent

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