Literature DB >> 25424967

Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

Aaron M Whittaker1, Vy M Dong.   

Abstract

By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amides; cross-coupling; dehydrogenation; esters; nickel

Mesh:

Substances:

Year:  2014        PMID: 25424967      PMCID: PMC4551080          DOI: 10.1002/anie.201410322

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  58 in total

1.  Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis.

Authors:  Satoru Kuwano; Shingo Harada; Raphaël Oriez; Ken-ichi Yamada
Journal:  Chem Commun (Camb)       Date:  2011-11-07       Impact factor: 6.222

2.  Synthesis of five- and six-membered benzocyclic ketones through intramolecular alkene hydroacylation catalyzed by nickel(0)/N-heterocyclic carbenes.

Authors:  Yoichi Hoshimoto; Yukari Hayashi; Haruka Suzuki; Masato Ohashi; Sensuke Ogoshi
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

3.  Palladium-catalyzed aerobic oxidative direct esterification of alcohols.

Authors:  Chao Liu; Jing Wang; Lingkui Meng; Yi Deng; Yao Li; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-07       Impact factor: 15.336

4.  Direct functionalization of tetrahydrofuran and 1,4-dioxane: nickel-catalyzed oxidative C(sp3)-H arylation.

Authors:  Dong Liu; Chao Liu; Heng Li; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-19       Impact factor: 15.336

5.  Nickel-catalyzed redox-economical coupling of alcohols and alkynes to form allylic alcohols.

Authors:  Kenichiro Nakai; Yuji Yoshida; Takuya Kurahashi; Seijiro Matsubara
Journal:  J Am Chem Soc       Date:  2014-05-20       Impact factor: 15.419

6.  Asymmetric synthesis of highly substituted β-lactones through oxidative carbene catalysis with LiCl as cooperative Lewis acid.

Authors:  Srikrishna Bera; Ramesh C Samanta; Constantin G Daniliuc; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-11       Impact factor: 15.336

7.  Nickel-catalyzed selective conversion of two different aldehydes to cross-coupled esters.

Authors:  Yoichi Hoshimoto; Masato Ohashi; Sensuke Ogoshi
Journal:  J Am Chem Soc       Date:  2011-03-15       Impact factor: 15.419

8.  Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde.

Authors:  Sensuke Ogoshi; Tomoya Arai; Masato Ohashi; Hideo Kurosawa
Journal:  Chem Commun (Camb)       Date:  2008-01-21       Impact factor: 6.222

9.  NHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of amines.

Authors:  Suman De Sarkar; Stefan Grimme; Armido Studer
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  Linear-selective hydroarylation of unactivated terminal and internal olefins with trifluoromethyl-substituted arenes.

Authors:  Joseph S Bair; York Schramm; Alexey G Sergeev; Eric Clot; Odile Eisenstein; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-09-15       Impact factor: 15.419

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  11 in total

1.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

2.  Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis.

Authors:  Paige E Piszel; Aristidis Vasilopoulos; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-24       Impact factor: 15.336

3.  Benchtop Delivery of Ni(cod)2 using Paraffin Capsules.

Authors:  Jacob E Dander; Nicholas A Weires; Neil K Garg
Journal:  Org Lett       Date:  2016-07-25       Impact factor: 6.005

Review 4.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

5.  Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters.

Authors:  Amira H Dardir; Patrick R Melvin; Ryan M Davis; Nilay Hazari; Megan Mohadjer Beromi
Journal:  J Org Chem       Date:  2017-12-12       Impact factor: 4.354

6.  Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp3)-H bonds.

Authors:  José A Fernández-Salas; Enrico Marelli; Steven P Nolan
Journal:  Chem Sci       Date:  2015-06-22       Impact factor: 9.825

7.  Chemoselective dehydrogenative esterification of aldehydes and alcohols with a dimeric rhodium(ii) catalyst.

Authors:  Junjie Cheng; Meijuan Zhu; Chao Wang; Junjun Li; Xue Jiang; Yawen Wei; Weijun Tang; Dong Xue; Jianliang Xiao
Journal:  Chem Sci       Date:  2016-03-29       Impact factor: 9.825

8.  Nickel-Catalyzed Arylation of Heteroaryl-containing Diarylmethanes: Exceptional Reactivity of the Ni(NIXANTPHOS)-based Catalyst.

Authors:  Xinyu Cao; Sheng-Chun Sha; Minyan Li; Byeong-Seon Kim; Catherine Morgan; Rudan Huang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-26       Impact factor: 9.825

9.  Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides.

Authors:  Zhao Wu; Kami L Hull
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

10.  Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions.

Authors:  Klara Čebular; Bojan Đ Božić; Stojan Stavber
Journal:  Molecules       Date:  2018-09-02       Impact factor: 4.411

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