Literature DB >> 25325885

1,3-Dicyclohexylimidazol-2-ylidene as a superior ligand for the nickel-catalyzed cross-couplings of aryl and benzyl methyl ethers with organoboron reagents.

Mamoru Tobisu1, Ayaka Yasutome, Hirotaka Kinuta, Keisuke Nakamura, Naoto Chatani.   

Abstract

A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.

Entities:  

Year:  2014        PMID: 25325885     DOI: 10.1021/ol502583h

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


  14 in total

1.  Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects.

Authors:  Kevin Wu; Abigail G Doyle
Journal:  Nat Chem       Date:  2017-03-06       Impact factor: 24.427

2.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

3.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

4.  Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

5.  Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

Authors:  Trevor D Lohrey; Alexander Q Cusumano; William A Goddard; Brian M Stoltz
Journal:  ACS Catal       Date:  2021-08-02       Impact factor: 13.700

6.  Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Authors:  Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2018-05-10       Impact factor: 6.005

7.  Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers and esters.

Authors:  Emily J Tollefson; Luke E Hanna; Elizabeth R Jarvo
Journal:  Acc Chem Res       Date:  2015-07-21       Impact factor: 22.384

8.  Cross-coupling polycondensation via C-O or C-N bond cleavage.

Authors:  Ze-Kun Yang; Ning-Xin Xu; Ryo Takita; Atsuya Muranaka; Chao Wang; Masanobu Uchiyama
Journal:  Nat Commun       Date:  2018-04-23       Impact factor: 14.919

9.  Half-sandwich nickel(II) complexes bearing 1,3-di(cycloalkyl)imidazol-2-ylidene ligands.

Authors:  Johnathon Yau; Kaarel E Hunt; Laura McDougall; Alan R Kennedy; David J Nelson
Journal:  Beilstein J Org Chem       Date:  2015-11-12       Impact factor: 2.883

10.  Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane.

Authors:  Mamoru Tobisu; Takuya Igarashi; Naoto Chatani
Journal:  Beilstein J Org Chem       Date:  2016-04-07       Impact factor: 2.883

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