Late Stage Benzylic C–H Fluorination with [<sup>18</sup>F]Fluoride for PET Imaging

Huang, Xiongyi; Liu, Wei; Ren, Hongliang; Neelamegam, Ramesh; Hooker, Jacob M.; Groves, John T.

doi:10.1021/ja5039819

Cited by 219 publications

(153 citation statements)

References 37 publications

(29 reference statements)

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“…99 By using Mn(salen)OTs (18) (Fig. 5) in the presence of PhIO (iodosylbenzene) as the oxidant, a variety of organic molecules and known drugs were labelled with 18 F with RCY ranging from 20% to 72% within 10 min.…”

Section: Manganese Fluoride Complexesmentioning

confidence: 99%

Transition metal complex assisted C_sp3–F bond formation

Lin

Weng

2015

Dalton Trans.

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Fluoroorganic compounds have attracted significant attention in various fields, such as pharmaceutical, agricultural chemistry, and materials science, as a result of their unique physical, chemical, and physiological properties. Consequently, extensive efforts have been devoted to the site-specific synthesis of organofluorine compounds. In recent years, transition-metal-mediated C-F bond formation has emerged as a powerful method for fabrication of these compounds. this Perspective mainly focuses on the most recent advances in transition-metal-assisted synthesis of alkyl fluorides.

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Section: Manganese Fluoride Complexesmentioning

confidence: 99%

Transition metal complex assisted C_sp3–F bond formation

Lin

Weng

2015

Dalton Trans.

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“…45) [74]. High radiochemical yields of C-H fluorination were described, for complex molecules with diverse functional groups, in fast reaction times (10 min).…”

Section: Oxidative Fluorination With Fluoridementioning

confidence: 99%

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Campbell

Hoover

Ritter

2014

Topics in Organometallic Chemistry

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The development of new C-F bond forming reactions from organotransition metal complexes has played a key role in advancing the field of fluorination chemistry and has allowed for improved access to fluorinated organic molecules of interest in medicine, materials, and agrochemicals. In this review, we describe the development of transition metal-mediated and metal-catalyzed fluorination methods over the past decade. Special attention is paid to the variety of organometallic mechanisms by which C-F bond formation can occur and the strengths and limitations of different approaches.

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“…Method without using transition-metal catalysts and organocatalysts has also been developed. [15] In addition, the research groups of Groves [16] and Carrol [17] have developed successful protocols for benzylic fluorination with 18 F fluoride for positron emission tomography (PET). However, the powerfulness of benzylic C-H fluorination has not been tested in any multi-step synthesis.…”

Section: Introductionmentioning

confidence: 99%

Application of Benzylic C-H Fluorination for the Formal Synthesis of syn-α, β-Difluoro-γ-amino Acid

刘清泉¹,

胡祥国²

2018

Chin. J. Org. Chem.

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Benzylic C-H fluorination has emerged as a valuable tool for the introduction of fluorine. However, the powerfulness of benzylic C-H fluorination has not been tested in any multi-step synthesis. α,β-Difluoro-γ-amino acids are useful entities for biological application owing to the so-called fluorine conformational effect. In this work, benzylic C-H fluorination has been successfully utilized as the key step for the formal synthesis of syn-α,β-difluoro-γ-amino acid 1, a very challenging but useful target. The approach developed in this work could be viewed as more practical compared to the previous one, because: (1) no corrosive and toxic nucleophilic fluorinating reagents are used, (2) the overall yield is 18% (the previous approach is about 5%), and (3) the key benzylic C-H reaction developed by Chen and co-workers was scaled up to one gram without decreasing its original efficiency. A striking fluorine effect was observed: a carbon with one fluorine atom on the adjacent carbon is much less reactive than an ordinary carbon for the benzylic C-H fluorination.

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Late Stage Benzylic C–H Fluorination with [¹⁸F]Fluoride for PET Imaging

Cited by 219 publications

References 37 publications

Transition metal complex assisted C_sp3–F bond formation

Transition metal complex assisted C_sp3–F bond formation

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Application of Benzylic C-H Fluorination for the Formal Synthesis of syn-α, β-Difluoro-γ-amino Acid

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Late Stage Benzylic C–H Fluorination with [18F]Fluoride for PET Imaging

Cited by 219 publications

References 37 publications

Transition metal complex assisted Csp3–F bond formation

Transition metal complex assisted Csp3–F bond formation

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Application of Benzylic C-H Fluorination for the Formal Synthesis of syn-α, β-Difluoro-γ-amino Acid

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Late Stage Benzylic C–H Fluorination with [¹⁸F]Fluoride for PET Imaging

Transition metal complex assisted C_sp3–F bond formation

Transition metal complex assisted C_sp3–F bond formation