Literature DB >> 11843586

Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system.

Alois Fürstner1, Günter Seidel.   

Abstract

[reaction: see text] Aryl chlorides bearing electron-withdrawing groups react with bis(pinacol)borane 1 to give aryl boronates in good to excellent yields in the presence of a catalyst formed in situ from Pd(OAc)(2) and the imidazolium chloride 2. The reaction is greatly accelerated when carried out under microwave heating.

Entities:  

Year:  2002        PMID: 11843586     DOI: 10.1021/ol0171463

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

1.  A rapid microwave protocol for Heck vinylation of aryl chlorides under air.

Authors:  Gopal K Datta; Karl S A Vallin; Mats Larhed
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

2.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

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.  Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

5.  Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336

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.  An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane.

Authors:  Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-06-25       Impact factor: 4.354

8.  Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: one step greener.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal:  Org Lett       Date:  2012-09-04       Impact factor: 6.005

9.  Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes.

Authors:  George Iakobson; Junyi Du; Alexandra M Z Slawin; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2015-08-26       Impact factor: 2.883

10.  Boron-rich benzene and pyrene derivatives for the detection of thermal neutrons.

Authors:  Henok A Yemam; Adam Mahl; Unsal Koldemir; Tyler Remedes; Sean Parkin; Uwe Greife; Alan Sellinger
Journal:  Sci Rep       Date:  2015-09-03       Impact factor: 4.379

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