(Radio)fluoroclick Reaction Enabled by a Hydrogen‐Bonding Cluster

Zeng, Xiaojun; Li, Junling; Ng, Chin K.; Hammond, Gerald B.; Xu, Bo

doi:10.1002/ange.201711341

Cited by 15 publications

(1 citation statement)

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“…52,53 An in-situ generated reactive halogenation reagent could be advantageous in such instances. [54][55][56][57][58][59] Recently, Oestreich and co-workers reported the hydroiodination of C-C multiple bonds by using in-situ-generated HI or HBr driven by the aromatization of cyclohexa-1,4-dienes. 60,61 We are now glad to report a…”

Section: Introductionmentioning

confidence: 99%

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Zeng

Liu

Yang

et al. 2020

Chem

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We describe a catalyst-free 1,2-trans-dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio-and stereoselectivity. This versatile dihalogenation system-a combination of NX 1 S electrophile and alkali metal halide (MX 2 ) in acetic acid-is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the in-situ generation of X 1 X 2 electrophile, including ICl, IBr, BrCl, I 2, and Br 2 .

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Section: Introductionmentioning

confidence: 99%

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Zeng

Liu

Yang

et al. 2020

Chem

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Synthesis of β‐Keto Sulfones by Oxy‐Sulfonylation of Alkynes in HFIP

Chen

Yan

et al. 2022

Adv Synth Catal

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Herein, we have established a method for the construction of β-keto sulfones through aerobic oxy-sulfonylation of alkynes with sulfinates. The reaction performed employing air as the oxidant and oxygen source. Moreover, this protocol exhibits low consume of sulfinates, short reaction period, and minimal waste. Mechanism study and density functional theory (DFT) calculation showed that the solvent played a significant role in the transformation.

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[¹⁸F]Fluorine‐Labeled Pharmaceuticals: Direct Aromatic Fluorination Compared to Multi‐Step Strategies

Krüll

Heinrich

2018

Asian J Org Chem

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Positron emission tomography (PET) presents an important tool for medicinal and pharmaceutical investigations, with applications ranging from fundamental research to the diagnosis of a broad variety of diseases. Crucial for the use of this technique is, however, a robust labeling strategy for the preparation of the required radiolabeled compound. For 18‐fluorine‐labeling, which represents the most widely applied method in this field, it is interesting to note that a kind of paradigm change occurred over the last years. While multi‐step labeling strategies were the preferred approach for many decades, mainly due to the lack of suitable leaving groups for direct [18F]fluorination reactions, the synthetic tools to achieve the highly attractive direct 18‐fluorine‐labeling rapidly increased recently. This focus review points out a comparison between the multi‐step approaches and the newly developed direct fluorination strategies available for nucleophilic 18‐fluorination of carbocyclic aromatic systems, including a discussion of advantages and limitations.

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(Radio)fluoroclick Reaction Enabled by a Hydrogen‐Bonding Cluster

Cited by 15 publications

References 86 publications

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Synthesis of β‐Keto Sulfones by Oxy‐Sulfonylation of Alkynes in HFIP

[¹⁸F]Fluorine‐Labeled Pharmaceuticals: Direct Aromatic Fluorination Compared to Multi‐Step Strategies

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(Radio)fluoroclick Reaction Enabled by a Hydrogen‐Bonding Cluster

Cited by 15 publications

References 86 publications

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Synthesis of β‐Keto Sulfones by Oxy‐Sulfonylation of Alkynes in HFIP

[18F]Fluorine‐Labeled Pharmaceuticals: Direct Aromatic Fluorination Compared to Multi‐Step Strategies

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[¹⁸F]Fluorine‐Labeled Pharmaceuticals: Direct Aromatic Fluorination Compared to Multi‐Step Strategies