Literature DB >> 23952320

Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides.

Shohei Sakashita1, Miho Takizawa, Juugaku Sugai, Hajime Ito, Yasunori Yamamoto.   

Abstract

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH2CH2OH (20 mol %) in anhydrous DMF without bases.

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Year:  2013        PMID： 23952320     DOI： 10.1021/ol402268g

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


  8 in total

1.  Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

2.  Electron-Poor, Fluoro-Containing Arylboronic Acids as Efficient Coupling Partners for Bis(1,5-cyclooctadiene)nickel(0)/Tricyclohexylphosphine-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates.

Authors:  Wen-Bo Chen; Chun-Hui Xing; Jie Dong; Qiao-Sheng Hu
Journal:  Adv Synth Catal       Date:  2016-06-07       Impact factor: 5.837

3.  Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

Authors:  James R Colombe; Sebastian Bernhardt; Christos Stathakis; Stephen L Buchwald; Paul Knochel
Journal:  Org Lett       Date:  2013-10-24       Impact factor: 6.005

4.  Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Org Lett       Date:  2016-08-18       Impact factor: 6.005

5.  Efficient Approach to Carbinol Derivatives through Palladium-Catalyzed Base-Free Addition of Aryltriolborates to Aldehydes.

Authors:  Kun Hu; Pengqing Ye; Qianqian Zhen; Xinrong Yao; Tong Xu; Yinlin Shao; Jiuxi Chen
Journal:  Molecules       Date:  2017-09-20       Impact factor: 4.411

6.  A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water.

Authors:  Arnaud Peramo; Ibrahim Abdellah; Shannon Pecnard; Julie Mougin; Cyril Martini; Patrick Couvreur; Vincent Huc; Didier Desmaële
Journal:  Molecules       Date:  2020-03-24       Impact factor: 4.411

7.  Suzuki-Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers.

Authors:  Saburo Kobayashi; Mayoh Ashiya; Takuya Yamamoto; Kenji Tajima; Yasunori Yamamoto; Takuya Isono; Toshifumi Satoh
Journal:  Polymers (Basel)       Date:  2021-11-28       Impact factor: 4.329

8.  Mild and Efficient Synthesis of Diverse Organo-AuI -L Complexes in Green Solvents.

Authors:  Fredric J L Ingner; Ann-Cathrin Schmitt; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  ChemSusChem       Date:  2020-03-03       Impact factor: 8.928
  8 in total

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