Literature DB >> 27410397

KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.

Kelsey C Miles1, M Leigh Abrams1, Clark R Landis1, Shannon S Stahl1.   

Abstract

A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.

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Year:  2016        PMID： 27410397      PMCID： PMC5279997          DOI： 10.1021/acs.orglett.6b01598

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


  24 in total

1.  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

Review 2.  Conversion of biomass into chemicals over metal catalysts.

Authors:  Michèle Besson; Pierre Gallezot; Catherine Pinel
Journal:  Chem Rev       Date:  2013-10-01       Impact factor: 60.622

3.  Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

Authors:  Thomas P Clark; Clark R Landis; Susan L Freed; Jerzy Klosin; Khalil A Abboud
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

4.  Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.

Authors:  Richard I McDonald; Gene W Wong; Ram P Neupane; Shannon S Stahl; Clark R Landis
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

5.  Highly efficient, organocatalytic aerobic alcohol oxidation.

Authors:  Masatoshi Shibuya; Yuji Osada; Yusuke Sasano; Masaki Tomizawa; Yoshiharu Iwabuchi
Journal:  J Am Chem Soc       Date:  2011-04-07       Impact factor: 15.419

6.  Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-11-01       Impact factor: 13.084

7.  Selective aerobic oxidation of alcohols to aldehydes, carboxylic acids, and imines catalyzed by a Ag-NHC complex.

Authors:  Lei Han; Ping Xing; Biao Jiang
Journal:  Org Lett       Date:  2014-06-17       Impact factor: 6.005

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.  Transition-metal-free: a highly efficient catalytic aerobic alcohol oxidation process.

Authors:  Renhua Liu; Xinmiao Liang; Chunyan Dong; Xinquan Hu
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

10.  Efficient NO equivalent for activation of molecular oxygen and its applications in transition-metal-free catalytic aerobic alcohol oxidation.

Authors:  Yi Xie; Weimin Mo; Dong Xu; Zhenlu Shen; Nan Sun; Baoxiang Hu; Xinquan Hu
Journal:  J Org Chem       Date:  2007-04-21       Impact factor: 4.354
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  1 in total

1.  Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.

Authors:  Juno C Siu; Joseph B Parry; Song Lin
Journal:  J Am Chem Soc       Date:  2019-01-28       Impact factor: 15.419
  1 in total

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