Boron-Substituted Difluorocyclopropanes:  New Building Blocks of <i>gem</i>-Difluorocyclopropanes

Fujioka, Yasutaka; Amii, Hideki

doi:10.1021/ol702851t

Cited by 68 publications

(33 citation statements)

References 44 publications

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“…[4] While anumber of efficient methods were known, few methods exist for the synthesis of gem-difluoroalkanes bearing easily transformable functional groups,w hich are important for allowing rapid assembly of complex fluorine-containing molecules in amodular fashion. [7] As such, gem-difluorinated alkylboron compounds [8] should serve as intriguing synthons for organofluorine synthesis.T his structural motif might also find applications in medicinal chemistry. [6] Besides,there has been an increase in the number of boron-containing drugs in which the boron motif is the key pharmacophore ( Figure 1b).…”

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confidence: 99%

gem‐Difluorination of Alkenyl N‐methyliminodiacetyl Boronates: Synthesis of α‐ and β‐Difluorinated Alkylborons

Lv,

Li,

et al. 2018

Angew Chem Int Ed

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Organofluorine compounds are widely used in pharmaceutical, agrochemical, and materials sciences.T he syntheses and applications of fluorinated organoborons facilitate the rapid and modular assemblies of fluorine-containing molecules because of the versatility of C À Bb onds in diverse chemical transformations.R eported herein is am igratory geminal difluorination of aryl-substituted alkenyl N-methyliminodiacetyl (MIDA) boronates using commercially available Py·HF as the fluorine source and hyperiodine as the oxidant. The protocol offers facile access to a-a nd bdifluorinated alkylboron compounds,b oth of which have previously been challenging to prepare.M ild reaction conditions,b road substrate scope,g ood functional-group tolerance,and moderate to good yields were observed. The utility of these products is demonstrated by further transformations of the CÀBbond into other valuable functional groups.

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confidence: 99%

gem‐Difluorination of Alkenyl N‐methyliminodiacetyl Boronates: Synthesis of α‐ and β‐Difluorinated Alkylborons

Lv,

Li,

et al. 2018

Angew Chem Int Ed

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“…Higher temperatures are often required for the generation as well as efficient reactions of difluorocarbene with alkenes. Some of the reagents used previously include sodium chlorodifluoroacetate (or sodium bromodifluoroacetate), [7] PhHgCF 3 [8] and Me 3 SnCF 3 [9] (Seyferth reagents), FSO 2 CF 2 CO 2 SiMe 3 (TFDA), [6h, 10] and Zn/CF 2 Br 2 . [11] However, most of these reagents suffer from disadvantages such as harsh reaction conditions, high toxicity, lack of commercial availability, and/ or low product yields.…”

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confidence: 99%

Synthesis of gem‐Difluorinated Cyclopropanes and Cyclopropenes: Trifluoromethyltrimethylsilane as a Difluorocarbene Source

et al. 2011

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“…22A). This strategy was also amenable to the stereospecific preparation of boron-substituted gem -difluorocyclopropanes [55], which could be rapidly transformed to afford functionalized gem -difluorocyclopropanes via lithium carbenoids or by subsequent oxidation (Fig. 22B).…”

Section: ) Fluorination By Decarboxylative Reagentsmentioning

confidence: 99%

Decarboxylative Fluorination Strategies for Accessing Medicinally- Relevant Products

Qiao¹,

Zhu²,

Ambler³

et al. 2014

CTMC

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Fluorinated organic compounds have a long history in medicinal chemistry, and synthetic methods to access target fluorinated compounds are undergoing a revolution. One powerful strategy for the installation of fluorine-containing functional groups includes decarboxylative reactions. Benefits of decarboxylative approaches potentially include: 1) readily available substrates or reagents 2) mild reaction conditions; 3) simplified purification. This focus review highlights the applications of decarboxylation strategies for fluorination reactions to access compounds with biomedical potential. The manuscript highlights on two general strategies, fluorination by decarboxylative reagents and by decarboxylation of substrates. Where relevant, examples of medicinally useful compounds that can be accessed using these strategies are highlighted.

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Boron-Substituted Difluorocyclopropanes: New Building Blocks of gem-Difluorocyclopropanes

Cited by 68 publications

References 44 publications

gem‐Difluorination of Alkenyl N‐methyliminodiacetyl Boronates: Synthesis of α‐ and β‐Difluorinated Alkylborons

gem‐Difluorination of Alkenyl N‐methyliminodiacetyl Boronates: Synthesis of α‐ and β‐Difluorinated Alkylborons

Synthesis of gem‐Difluorinated Cyclopropanes and Cyclopropenes: Trifluoromethyltrimethylsilane as a Difluorocarbene Source

Decarboxylative Fluorination Strategies for Accessing Medicinally- Relevant Products

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