Literature DB >> 15548040

Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis.

Pierre-Emmanuel Broutin1, Igor Cerna, Maria Campaniello, Frédéric Leroux, Françoise Colobert.   

Abstract

The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc)(2) together with DPEphos as ligand and Et(3)N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields. [reaction: see text]

Entities:  

Year:  2004        PMID: 15548040     DOI: 10.1021/ol048303b

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


  7 in total

1.  Suzuki-Miyaura cross-coupling of 3-pyridyl triflates with 1-alkenyl-2-pinacol boronates.

Authors:  James R Vyvyan; Jennifer A Dell Née Meyer; Toby J Ligon; Kelsey K Motanic; Hayley S Wall
Journal:  Synthesis (Stuttg)       Date:  2010-11       Impact factor: 3.157

2.  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

3.  Syntheses of novel diaryl[d,f ][1,3]diazepines via one-pot Suzuki coupling followed by direct ring closure with carboxylic acids.

Authors:  Longjia Yan; Xin Che; Xu Bai; Yazhong Pei
Journal:  Mol Divers       Date:  2012-07-01       Impact factor: 2.943

4.  Synthesis and Evaluation of Pyridyloxypyridyl Indole Carboxamides as Potential PET Imaging Agents for 5-HT2C Receptors.

Authors:  Fanxing Zeng; Jonathon A Nye; Ronald J Voll; Leonard Howell; Mark M Goodman
Journal:  ACS Med Chem Lett       Date:  2018-02-05       Impact factor: 4.345

5.  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

6.  Unexpected Vulnerability of DPEphos to C-O Activation in the Presence of Nucleophilic Metal Hydrides.

Authors:  Mateusz K Cybulski; Nicholas A Beattie; Stuart A Macgregor; Mary F Mahon; Michael K Whittlesey
Journal:  Chemistry       Date:  2020-07-28       Impact factor: 5.236

7.  Concise Syntheses of Marine (Bis)indole Alkaloids Meridianin C, D, F, and G and Scalaridine A via One-Pot Masuda Borylation-Suzuki Coupling Sequence.

Authors:  Marco Kruppa; Gereon A Sommer; Thomas J J Müller
Journal:  Molecules       Date:  2022-03-30       Impact factor: 4.411

  7 in total

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