Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes.
electro-oxidative acetalization
electro-oxidative coupling
electro-oxidative esterification
oxidative esterification
phosphonium electrolytes
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
19 Feb 2021
19 Feb 2021
Historique:
received:
01
12
2020
pubmed:
8
12
2020
medline:
8
12
2020
entrez:
7
12
2020
Statut:
ppublish
Résumé
A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.
Identifiants
pubmed: 33283370
doi: 10.1002/chem.202005158
pmc: PMC7986861
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3682-3687Subventions
Organisme : European Research Council
ID : ERC project 716136: 2O2ACTIVATION
Pays : International
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
Références
Org Lett. 2010 Aug 20;12(16):3645-7
pubmed: 20669896
J Am Chem Soc. 2010 Feb 3;132(4):1190-1
pubmed: 20055393
Angew Chem Int Ed Engl. 2011 May 23;50(22):5144-8
pubmed: 21480446
J Am Chem Soc. 2009 Mar 11;131(9):3146-7
pubmed: 19216551
J Org Chem. 2011 May 6;76(9):3016-23
pubmed: 21449617
Org Lett. 2015 Aug 7;17(15):3666-9
pubmed: 26161512
Angew Chem Int Ed Engl. 2018 May 22;57(21):6018-6041
pubmed: 29359378
Bioresour Technol. 2010 Aug;101(15):6225-9
pubmed: 20304633
Org Lett. 2020 Jul 2;22(13):4927-4931
pubmed: 32383888
Org Lett. 2013 Oct 4;15(19):5072-5
pubmed: 24050194
J Am Chem Soc. 2008 Mar 5;130(9):2754-5
pubmed: 18257577
Nat Commun. 2020 Jun 1;11(1):2706
pubmed: 32483217
Phytochemistry. 2006 Jul;67(13):1347-52
pubmed: 16814820
Angew Chem Int Ed Engl. 2012 Jul 16;51(29):7259-62
pubmed: 22689181
Dalton Trans. 2014 Sep 28;43(36):13460-70
pubmed: 25058479
Org Biomol Chem. 2018 May 2;16(17):3114-3120
pubmed: 29469910
Chem Commun (Camb). 2005 Mar 14;(10):1303-5
pubmed: 15742059
Angew Chem Int Ed Engl. 2018 May 14;57(20):5594-5619
pubmed: 29292849
ChemSusChem. 2012 Oct;5(10):1892-6
pubmed: 23001838
J Agric Food Chem. 2012 Jan 11;60(1):112-23
pubmed: 22148226
Chemistry. 2021 Feb 19;27(11):3682-3687
pubmed: 33283370
ChemSusChem. 2019 Jul 5;12(13):2898-2910
pubmed: 30934144
Org Lett. 2000 Mar 9;2(5):577-9
pubmed: 10814382
Chem Sci. 2016 Jul 1;7(7):4428-4434
pubmed: 30155090
Acc Chem Res. 2014 Apr 15;47(4):1054-66
pubmed: 24661043
Nature. 2015 Aug 6;524(7563):79-83
pubmed: 26200342
Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1312-5
pubmed: 25424967
Chem Commun (Camb). 2012 Apr 7;48(28):3448-50
pubmed: 22358109
Angew Chem Int Ed Engl. 2012 Jun 4;51(23):5662-6
pubmed: 22539112
J Am Chem Soc. 2017 Jan 18;139(2):811-818
pubmed: 28006898
Org Lett. 2006 Mar 16;8(6):1121-4
pubmed: 16524283
J Am Chem Soc. 2009 Apr 29;131(16):5738-9
pubmed: 19338301
Angew Chem Int Ed Engl. 2011 May 23;50(22):5139-43
pubmed: 21523865