Literature DB >> 19533703

A facile route to aryl boronates: room-temperature, copper-catalyzed borylation of aryl halides with alkoxy diboron reagents.

Christian Kleeberg1, Li Dang, Zhenyang Lin, Todd B Marder.   

Abstract

A simple but effective copper-catalyzed borylation of aryl halides, including electron-rich and sterically hindered aryl bromides, with alkoxy diboron reagents occurs under mild conditions (see scheme). Preliminary DFT studies of the mechanism suggest that sigma-bond metathesis between a copper-boryl intermediate and the aryl halide generates the aryl boronate product.

Entities:  

Year:  2009        PMID: 19533703     DOI: 10.1002/anie.200901879

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


  32 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

Review 2.  Catalysis in service of main group chemistry offers a versatile approach to p-block molecules and materials.

Authors:  Erin M Leitao; Titel Jurca; Ian Manners
Journal:  Nat Chem       Date:  2013-10       Impact factor: 24.427

3.  Miyaura Borylations of Aryl Bromides in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Ralph Moser; Karl R Voigtritter
Journal:  Isr J Chem       Date:  2010-12-01       Impact factor: 3.333

4.  New Molecular Scaffolds for Fluorescent Voltage Indicators.

Authors:  Steven C Boggess; Shivaani S Gandhi; Brian A Siemons; Nathaniel Huebsch; Kevin E Healy; Evan W Miller
Journal:  ACS Chem Biol       Date:  2019-02-08       Impact factor: 5.100

5.  Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II).

Authors:  Amanda E King; Bradford L Ryland; Thomas C Brunold; Shannon S Stahl
Journal:  Organometallics       Date:  2012-08-24       Impact factor: 3.876

6.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

7.  Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Green Chem       Date:  2014-08-01       Impact factor: 10.182

8.  Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration.

Authors:  R David Grigg; Ryan Van Hoveln; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-09-19       Impact factor: 15.419

9.  Cu(I)-catalyzed (11)C carboxylation of boronic acid esters: a rapid and convenient entry to (11)C-labeled carboxylic acids, esters, and amides.

Authors:  Patrick J Riss; Shuiyu Lu; Sanjay Telu; Franklin I Aigbirhio; Victor W Pike
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

10.  Coligand role in the NHC nickel catalyzed C-F bond activation: investigations on the insertion of bis(NHC) nickel into the C-F bond of hexafluorobenzene.

Authors:  Maximilian W Kuntze-Fechner; Hendrik Verplancke; Lukas Tendera; Martin Diefenbach; Ivo Krummenacher; Holger Braunschweig; Todd B Marder; Max C Holthausen; Udo Radius
Journal:  Chem Sci       Date:  2020-10-06       Impact factor: 9.825

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