Literature DB >> 14692753

A general method for the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides: synthesis of di- and tri-ortho-substituted biaryls in 2-propanol at room temperature.

Oscar Navarro1, Roy A Kelly, Steven P Nolan.   

Abstract

The catalytic formation of di- and trisubstituted ortho biaryl junctions has been achieved using a palladacylce pre-catalyst bearing a N-heterocyclic carbene ligand. This transformation is performed at room temperature in technical grade 2-propanol.

Entities:  

Year:  2003        PMID： 14692753     DOI： 10.1021/ja038631r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

1.  Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors:  Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

3.  [(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions.

Authors:  Qinqin Xia; Shicheng Shi; Pengcheng Gao; Roger Lalancette; Roman Szostak; Michal Szostak
Journal:  J Org Chem       Date:  2021-10-07       Impact factor: 4.198

4.  Synthesis of hindered biphenyls by sequential non-transition metal-catalyzed reaction/palladium-catalyzed cross-couplings.

Authors:  Ping He; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2008-03-17       Impact factor: 2.415

5.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

6.  Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.

Authors:  Guangming Nan; Fang Ren; Meiming Luo
Journal:  Beilstein J Org Chem       Date:  2010-06-28       Impact factor: 2.883

7.  Palladium-catalyzed cross-coupling reactions of organosilanols and their salts: practical alternatives to boron- and tin-based methods.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  Triphenylphosphine as a ligand for room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl chlorides with arylboronic acids.

Authors:  Zhen-Yu Tang; Qiao-Sheng Hu
Journal:  J Org Chem       Date:  2006-03-03       Impact factor: 4.354

9.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Effects of Bases and Halides on the Amination of Chloroarenes Catalyzed by Pd(PtBu3)2.

Authors:  Shashank Shekhar; John F Hartwig
Journal:  Organometallics       Date:  2006-12-19       Impact factor: 3.876
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