Literature DB >> 24214845

Synthesis and applications of α-trifluoromethylated alkylboron compounds.

O Andreea Argintaru1, DaWeon Ryu, Ioana Aron, Gary A Molander.   

Abstract

RBF3 K is a chemist's BFF: A metal-free synthetic route to unprecedented organoboron compounds bearing an α-trifluoromethyl substituent, employing a variety of trifluoroborate (RBF3 K) starting materials, is reported. These substrates represent the first isolated α-trifluoromethylated alkylboron building blocks, and these reagents lead to a variety of useful bench-stable, synthetic intermediates. Pin=pinacol.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; diazo compounds; silanes; synthetic methods; trifluoromethylation

Mesh：

Substances：

Year:  2013        PMID： 24214845      PMCID： PMC3904770          DOI： 10.1002/anie.201308036

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  51 in total

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Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Org Lett       Date:  2012-04-12       Impact factor: 6.005

3.  Silver-catalyzed hydrotrifluoromethylation of unactivated alkenes with CF3SiMe3.

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4.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

5.  Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.

Authors:  Phong V Pham; David A Nagib; David W C MacMillan
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6.  An exceptional hydroboration of substituted fluoroolefins providing tertiary alcohols.

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Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

7.  Rh-catalyzed addition of β-carbonyl pinacol alkylboronates to aldehydes: asymmetric synthesis of γ-butyrolactones.

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Journal:  Org Lett       Date:  2013-06-17       Impact factor: 6.005

8.  A Weinreb amide approach to the synthesis of trifluoromethylketones.

Authors:  DiAndra M Rudzinski; Christopher B Kelly; Nicholas E Leadbeater
Journal:  Chem Commun (Camb)       Date:  2012-10-07       Impact factor: 6.222

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10.  Conversion of alkyltrifluoroborates into alkyldichloroboranes with tetrachlorosilane in coordinating solvents.

Authors:  Byung Ju Kim; Donald S Matteson
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-07       Impact factor: 15.336
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3.  Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis.

Authors:  Yohei Yamashita; John C Tellis; Gary A Molander
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4.  Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors:  Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
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5.  Transition-Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives.

Authors:  Chen Zhu; John R Falck
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

6.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors:  Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

7.  A multicomponent approach for the preparation of homoallylic alcohols.

Authors:  Jian-Siang Poh; Shing-Hing Lau; Iain G Dykes; Duc N Tran; Claudio Battilocchio; Steven V Ley
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8.  One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids.

Authors:  Venkata S Sadu; Hye-Rin Bin; Do-Min Lee; Kee-In Lee
Journal:  Sci Rep       Date:  2017-03-21       Impact factor: 4.379

9.  Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.

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10.  Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.

Authors:  Claudio Bomio; Mikhail A Kabeshov; Arthur R Lit; Shing-Hing Lau; Janna Ehlert; Claudio Battilocchio; Steven V Ley
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