Literature DB >> 25414624

Transition-Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives.

Chen Zhu1, John R Falck2.   

Abstract

Arylboronic acids and their derivatives have been widely exploited as important synthetic precursors in organic synthesis, materials science, and pharmaceutical development. In addition to numerous applications in transition-metal-mediated cross-coupling reactions, transition-metal-free transformations involving arylboronic acids and derivatives have recently received a surge of attention for converting the C-B bond to C-C, C-N, C-O, and many other C-X bonds. Consequently, a wide range of useful compounds, e.g., phenols, anilines, nitroarenes, and haloarenes, have been readily synthesized. Amongst these efforts, many versatile reagents have been developed and a lot of practical approaches demonstrated. The research in this promising field is summarized in the current review and organized on the basis of the type of bonds being formed.

Entities:  

Keywords:  Amination; Arylboronic acid; Halogenation; Hydroxylation; Transition-metal-free

Year:  2014        PMID: 25414624      PMCID: PMC4233718          DOI: 10.1002/adsc.201400305

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN: 1615-4150            Impact factor:   5.837


  30 in total

1.  Electrochemical hydroxylation of organoboron compounds.

Authors:  Kohei Hosoi; Yu Kuriyama; Shinsuke Inagi; Toshio Fuchigami
Journal:  Chem Commun (Camb)       Date:  2010-01-08       Impact factor: 6.222

2.  Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides.

Authors:  Chen Zhu; Rui Wang; J R Falck
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

3.  Photochemically promoted transition metal-free cross-coupling of acylsilanes with organoboronic esters.

Authors:  Kazuta Ito; Hiroto Tamashima; Nobuharu Iwasawa; Hiroyuki Kusama
Journal:  J Am Chem Soc       Date:  2011-02-23       Impact factor: 15.419

4.  Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Authors:  Helen K Scott; Varinder K Aggarwal
Journal:  Chemistry       Date:  2011-11-03       Impact factor: 5.236

5.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

6.  Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones.

Authors:  José Barluenga; María Tomás-Gamasa; Fernando Aznar; Carlos Valdés
Journal:  Nat Chem       Date:  2009-08-16       Impact factor: 24.427

7.  Electrophilic aromatic substitutions of aryltrifluoroborates with retention of the BF3- group: quantification of the activating and directing effects of the trifluoroborate group.

Authors:  Guillaume Berionni; Varvara Morozova; Maximilian Heininger; Peter Mayer; Paul Knochel; Herbert Mayr
Journal:  J Am Chem Soc       Date:  2013-04-12       Impact factor: 15.419

8.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors:  Scott N Mlynarski; Alexander S Karns; James P Morken
Journal:  J Am Chem Soc       Date:  2012-09-24       Impact factor: 15.419

9.  Arylation and vinylation of alpha-diazocarbonyl compounds with boroxines.

Authors:  Cheng Peng; Wei Zhang; Guobing Yan; Jianbo Wang
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

10.  The first general route for efficient synthesis of 18O labelled alcohols using the HOF·CH3CN complex.

Authors:  Julia Gatenyo; Inna Vints; Shlomo Rozen
Journal:  Chem Commun (Camb)       Date:  2013-08-28       Impact factor: 6.222

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  9 in total

1.  Electrochemical borylation of carboxylic acids.

Authors:  Lisa M Barton; Longrui Chen; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

2.  Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions.

Authors:  Sumbal Saba; Giancarlo Vaccari Botteselle; Marcelo Godoi; Tiago Elias Allievi Frizon; Fábio Zazyki Galetto; Jamal Rafique; Antonio L Braga
Journal:  Molecules       Date:  2017-08-18       Impact factor: 4.411

3.  Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis.

Authors:  Shuqing Chen; Peng Wang; Hong-Gang Cheng; Chihui Yang; Qianghui Zhou
Journal:  Chem Sci       Date:  2019-07-23       Impact factor: 9.825

4.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

5.  The graphite-catalyzed ipso-functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes.

Authors:  Anshu Dandia; Ruchi Sharma; Pratibha Saini; Ranveer Singh Badgoti; Kuldeep S Rathore; Vijay Parewa
Journal:  RSC Adv       Date:  2021-05-19       Impact factor: 4.036

6.  Catalyst- and solvent-free ipso-hydroxylation of arylboronic acids to phenols.

Authors:  Xiufang Yang; Xulu Jiang; Weitao Wang; Qi Yang; Yangmin Ma; Kuan Wang
Journal:  RSC Adv       Date:  2019-10-25       Impact factor: 4.036

7.  Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group.

Authors:  Tatjana Kreisel; Marvin Mendel; Adele E Queen; Kristina Deckers; Daniel Hupperich; Julian Riegger; Christoph Fricke; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-21       Impact factor: 16.823

8.  One-Pot Iridium Catalyzed C-H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes.

Authors:  Ghayoor A Chotana; Jose R Montero Bastidas; Susanne L Miller; Milton R Smith; Robert E Maleczka
Journal:  Molecules       Date:  2020-04-10       Impact factor: 4.411

9.  Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations.

Authors:  Christoph Fricke; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-20       Impact factor: 16.823

  9 in total

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