Hydroarylation of Alkenes Using Anilines in Hexafluoroisopropanol | Semantic Scholar (2024)

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@article{Colomer2020HydroarylationOA, title={Hydroarylation of Alkenes Using Anilines in Hexafluoroisopropanol}, author={Ignacio Colomer}, journal={ACS Catalysis}, year={2020}, volume={10}, pages={6023-6029}, url={https://api.semanticscholar.org/CorpusID:218926491}}
  • Ignacio Colomer
  • Published 12 May 2020
  • Chemistry
  • ACS Catalysis

Providing new methods for the selective functionalization of small molecules is highly desirable, because installing molecular diversity in a desired position, for example, allows one to modulate b...

48 Citations

48 Citations

Lewis Acid/Hexafluoroisopropanol: A Promoter System for Selective ortho-C-Alkylation of Anilines with Deactivated Styrene Derivatives and Unactivated Alkenes
    Shengdong WangGuillaume Force David Lebœuf

    Chemistry

    ACS Catalysis

  • 2020

Aniline derivatives are frequently encountered in molecules of industrial relevance such as dyes or antioxidants, which make the development of synthetic methods for the functionalization of these ...

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Regio- and Stereoselective Hexafluoroisopropoxylation and Trifluoroethoxylation of Allenamides.
    Dhananjay ChaudharyMalleswara Rao Kuram

    Chemistry

    The Journal of organic chemistry

  • 2024

Incorporating fluorinated moieties into organic molecules is an attractive strategy to enhance drug-like properties. Herein, we have developed a simple and self-promoted protocol for

A Highly Diastereoselective Spiro-Cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides
    Jie HuangShaofa Sun Gangqiang Wang

    Chemistry

    New Journal of Chemistry

  • 2021

A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developed via a base-induced annulation. This efficient and simple

  • 1
Difunctionalization Processes Enabled by Hexafluoroisopropanol
    Maciej PiejkoJ. MoranDavid Lebœuf

    Chemistry

  • 2024

In the past 5 years, hexafluoroisopropanol (HFIP) has been used as a unique solvent or additive to enable challenging transformations through substrate activation and stabilization of reactive

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Boron-Catalyzed Hydroarylation of 1,3-Dienes with Arylamines.
    Gautam KumarZheng‐Wang QuS. GrimmeIndranil Chatterjee

    Chemistry

    Organic letters

  • 2021

Catalytic hydroarylation reactions of conjugated dienes are achieved using tris(pentafluorophenyl)borane as a Lewis acid catalyst under mild reaction conditions. This new protocol shows a broad

  • 2
Benzylic C-H addition of aromatic amines to alkenes using a scandium catalyst.
    Jianhong SuYun‐Cheng LuoXin Xu

    Chemistry

    Chemical communications

  • 2021

An efficient and selective benzylic C(sp3)-H addition of o-CH3-substituted tertiary aromatic amines to alkenes has been achieved using an anilido-oxazoline ligand supported scandium catalyst, which

  • 1
AgNTf2-Catalyzed Regioselective C-H Alkenylation of N,N-Dialkylanilines with Ynamides.
    X. NieZhuo-Ya MaoJiawen GuoChangmei SiBangguo WeiG. Lin

    Chemistry

    The Journal of organic chemistry

  • 2022

This approach represents a facile hydroarylation of ynamides, allowing for the introduction of an alkenyl group exclusively at the para position of aniline derivatives, and a series of 4-alkenyl N,N-dialkylanilines were synthesized with excellent regioselectivities.

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Route to Functionalized Tetrahydrobenzo[d]azepines via Re2O7-Mediated Intramolecular Friedel-Crafts Reaction.
    Yuzhu ZhengQing HuangXiong FangYouwei Xie

    Chemistry

    The Journal of organic chemistry

  • 2024

We describe a Re2O7-mediated intramolecular dehydrative Friedel-Crafts reaction for the efficient synthesis of various benzo-fused heterocycles such as benzazepines and benzazocines. This process is

Current Advances in Meerwein-type Radical Alkene Functionalizations
    M. HeinrichNina Diesendorf

    Chemistry

    Synthesis

  • 2022

Alkene functionalizations via Meerwein arylations are becoming increasingly attractive, especially since a variety of mild and sustainable methods for aryl radical generation are available today.

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Acid–solvent cluster-catalyzed general and regioselective Friedel–Crafts arylation of alcohols
    Wanting FuJunkai Fu Zikun Wang

    Chemistry

    Organic Chemistry Frontiers

  • 2024

An acid–solvent clusters-catalyzed general and regioselective Friedel–Crafts alkylation has been described.

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The new magnesium-catalyzed reaction allows the use of a wide range of alkynes and anilines with different electronic and steric properties and provides free as well as protected aniline yields with excellent yields.

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The stereoselective intra- and intermolecular Friedel-Crafts alkylation of electron-rich arenes with epoxides can take place in refluxing 1,1,1,3,3,3-hexafluoroisopropanol owing to its weak acidity

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A highly para-selective copper(II)-catalyzed direct arylation of aniline and phenol derivatives.
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The ubiquity of the biaryl motif in natural products, medicines, and novel materials ensures a constant demand for their efficient and selective synthesis, and it is surprising that few para-selective direct arylation reactions are known.

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An efficient para-alkylation of primary and secondary anilines with a variety of sterically encumbered alkenes using a simple β-diketiminato scandium catalyst is reported. This protocol features 100%

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Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction.
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The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.

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HBF4- and AgBF4-Catalyzed ortho-Alkylation of Diarylamines and Phenols
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A silver-tetrafluoroborate- or HBF4-catalyzed ortho-alkylation reaction of phenols and diarylamines with styrenes has been explored. A broad substrate scope is presented as well as mechanistic

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Room Temperature Catalyst System for the Hydroarylation of Olefins.
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A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described, which is high yielding and is amenable to scale-up protocols.

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Gold-catalyzed hydroarylation of alkenes with dialkylanilines.
    Xingbang HuDavid MartinM. MelaimiG. Bertrand

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Anti-Bredt di(amino)carbene supported gold(I) chloride complexes are readily prepared in two steps from the corresponding isocyanide complexes. In the presence of KB(C6F5)4 as chloride scavenger,

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Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation.
    Ignacio ColomerR. C. BarcelosK. ChristensenT. Donohoe

    Chemistry

    Organic letters

  • 2016

Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.

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Hydroarylation of alkenes by protonation/Friedel-Crafts trapping - HFIP-mediated access to per-aryl quaternary stereocentres.
    C. NielsenAndrew J. P. WhiteDavid A. SaleJ. BurésA. Spivey

    Chemistry

    The Journal of organic chemistry

  • 2019

Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Brønsted bases and protonate to give carbocations which can be trapped by electron-rich arenes. The reaction

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