Literature DB >> 27171973

Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines.

Susan L Zultanski1, Jingyi Zhao1, Shannon S Stahl1.   

Abstract

A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.

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Year:  2016        PMID： 27171973      PMCID： PMC5273591          DOI： 10.1021/jacs.6b03931

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


  32 in total

1.  Catalyzed dehydrogenative coupling of primary alcohols with water, methanol, or amines.

Authors:  Theo Zweifel; Jean-Valère Naubron; Hansjörg Grützmacher
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems.

Authors:  Janelle E Steves; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-10-15       Impact factor: 15.419

3.  Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature.

Authors:  Jinho Kim; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-07-05       Impact factor: 13.084

4.  Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of H2 catalyzed by ruthenium pincer complexes: ligand-controlled selectivity.

Authors:  Boopathy Gnanaprakasam; Ekambaram Balaraman; Yehoshoa Ben-David; David Milstein
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-26       Impact factor: 15.336

Review 5.  Metal-catalysed approaches to amide bond formation.

Authors:  C Liana Allen; Jonathan M J Williams
Journal:  Chem Soc Rev       Date:  2011-03-17       Impact factor: 54.564

Review 6.  Rethinking amide bond synthesis.

Authors:  Vijaya R Pattabiraman; Jeffrey W Bode
Journal:  Nature       Date:  2011-12-21       Impact factor: 49.962

7.  A TEMPO-free copper-catalyzed aerobic oxidation of alcohols.

Authors:  Boran Xu; Jean-Philip Lumb; Bruce A Arndtsen
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-10       Impact factor: 15.336

8.  Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant.

Authors:  Laura M Dornan; Qun Cao; James C A Flanagan; James J Crawford; Matthew J Cook; Mark J Muldoon
Journal:  Chem Commun (Camb)       Date:  2013-07-11       Impact factor: 6.222

9.  Iron-catalysed oxidative amidation of alcohols with amines.

Authors:  Silvia Gaspa; Andrea Porcheddu; Lidia De Luca
Journal:  Org Biomol Chem       Date:  2013-06-21       Impact factor: 3.876

10.  Amide synthesis from alcohols and amines by the extrusion of dihydrogen.

Authors:  Lars Ulrik Nordstrøm; Henning Vogt; Robert Madsen
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419
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  6 in total

Review 1.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

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.  CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides.

Authors:  Kengo Kataoka; Keiju Wachi; Xiongjie Jin; Kosuke Suzuki; Yusuke Sasano; Yoshiharu Iwabuchi; Jun-Ya Hasegawa; Noritaka Mizuno; Kazuya Yamaguchi
Journal:  Chem Sci       Date:  2018-05-07       Impact factor: 9.825

4.  NH3⋅H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water.

Authors:  Guofu Zhang; Danting Ma; Yiyong Zhao; Guihua Zhang; Guangyao Mei; Jinghui Lyu; Chengrong Ding; Shang Shan
Journal:  ChemistryOpen       Date:  2018-11-13       Impact factor: 2.911

5.  Catalytic behaviour of the Cu(i)/L/TEMPO system for aerobic oxidation of alcohols - a kinetic and predictive model.

Authors:  Afnan Al-Hunaiti; Batool Abu-Radaha; Darren Wraith; Timo Repo
Journal:  RSC Adv       Date:  2022-03-10       Impact factor: 3.361

6.  Ground-state dioxygen undergoes metal-free [3 + 2]-annulations with allenes and nitrosoarenes under ambient conditions.

Authors:  Jinxian Liu; Manisha Skaria; Pankaj Sharma; Yun-Wei Chiang; Rai-Shung Liu
Journal:  Chem Sci       Date:  2017-05-24       Impact factor: 9.825
  6 in total

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