Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids.

decarboxylation polyfluoroarylation defluorinative alkylation late-stage functionalization photoredox catalysis radical reaction

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
03 05 2021
Historique:
received: 23 11 2020
pubmed: 23 1 2021
medline: 23 1 2021
entrez: 22 1 2021
Statut: ppublish

Résumé

Polyfluoroarenes are useful building blocks in several areas such as drug discovery, materials, and crop protection. Herein, we report the first polyfluoroarylation of aliphatic carboxylic acids via photoredox decarboxylation. The method proceeds with broad substrate scope and high functional group tolerance. Moreover, small complex molecules such as natural products and drugs can be modified by late-stage modification.

Identifiants

pubmed: 33481305
doi: 10.1002/anie.202015596
pmc: PMC8252513
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

10557-10562

Informations de copyright

© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Références

Chem Soc Rev. 2011 Jul;40(7):3496-508
pubmed: 21448484
Pest Manag Sci. 2017 Jun;73(6):1053-1066
pubmed: 28145087
Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7266-7270
pubmed: 28514050
Dalton Trans. 2010 Nov 21;39(43):10362-74
pubmed: 20938555
ACS Catal. 2017 Apr 7;7(4):2563-2575
pubmed: 28413692
Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1876-80
pubmed: 26695120
Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11196-9
pubmed: 26149104
J Am Chem Soc. 2016 Mar 16;138(10):3596-606
pubmed: 26942551
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
Chem Rev. 2015 Jan 28;115(2):612-33
pubmed: 25474722
Angew Chem Int Ed Engl. 2011 Jun 20;50(26):5918-23
pubmed: 21591032
Science. 2014 Jul 25;345(6195):437-40
pubmed: 24903563
Acc Chem Res. 2016 Oct 18;49(10):2273-2283
pubmed: 27682342
Org Biomol Chem. 2013 Apr 21;11(15):2387-403
pubmed: 23426621
Org Lett. 2007 Jul 5;9(14):2721-4
pubmed: 17559221
Chemistry. 2019 Sep 12;25(51):11797-11819
pubmed: 31099931
Nature. 2018 Feb 21;554(7693):511-514
pubmed: 29469096
Science. 2014 Feb 28;343(6174):1239176
pubmed: 24578578
J Am Chem Soc. 2006 Jun 7;128(22):7134-5
pubmed: 16734446
J Am Chem Soc. 2019 Feb 20;141(7):3187-3197
pubmed: 30681846
J Am Chem Soc. 2010 Mar 3;132(8):2522-3
pubmed: 20131777
Chem Rev. 2014 Feb 26;114(4):2432-506
pubmed: 24299176
Nature. 2018 Jul;559(7712):83-88
pubmed: 29925943
Angew Chem Int Ed Engl. 2019 Oct 14;58(42):14824-14848
pubmed: 30759327
J Org Chem. 2016 Aug 19;81(16):6898-926
pubmed: 27477076
Chem Soc Rev. 2011 Jan;40(1):102-13
pubmed: 20532341
J Am Chem Soc. 2015 Sep 9;137(35):11340-8
pubmed: 26291730
Chem Commun (Camb). 2007 Mar 14;(10):1003-22
pubmed: 17325792
J Am Chem Soc. 2013 Aug 14;135(32):12122-34
pubmed: 23859263
J Am Chem Soc. 2010 Sep 22;132(37):12850-2
pubmed: 20804140
Acc Chem Res. 2011 May 17;44(5):333-48
pubmed: 21410234
Angew Chem Int Ed Engl. 2015 Apr 7;54(15):4669-72
pubmed: 25690761
Angew Chem Int Ed Engl. 2021 May 3;60(19):10557-10562
pubmed: 33481305
Chem Rev. 2009 May;109(5):2119-83
pubmed: 19331346
Nat Chem. 2018 Dec;10(12):1229-1233
pubmed: 30297751
J Am Chem Soc. 2014 Feb 26;136(8):3002-5
pubmed: 24547940
Chem Rev. 2016 Sep 14;116(17):9850-913
pubmed: 27070820
J Am Chem Soc. 2010 May 26;132(20):6935-7
pubmed: 20438052
Nature. 2011 Dec 8;480(7376):224-8
pubmed: 22158245
J Med Chem. 2018 Jul 26;61(14):5822-5880
pubmed: 29400967
Chem Rev. 2015 Sep 9;115(17):9073-174
pubmed: 25854146
J Am Chem Soc. 2018 May 16;140(19):6083-6087
pubmed: 29634250
J Am Chem Soc. 2008 Jan 30;130(4):1128-9
pubmed: 18181627
Chem Commun (Camb). 2019 Mar 19;55(24):3489-3492
pubmed: 30829348
Chem Rev. 2018 Aug 22;118(16):7532-7585
pubmed: 30011194
Chem Sci. 2016 Nov 18;7(11):6796-6802
pubmed: 28042465
Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8214-64
pubmed: 23873766
J Am Chem Soc. 2020 Apr 22;142(16):7487-7496
pubmed: 32233362
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):532-536
pubmed: 30395385
Chembiochem. 2004 May 3;5(5):571-89
pubmed: 15122630
Science. 2013 Nov 22;342(6161):956-60
pubmed: 24264986
J Am Chem Soc. 2010 Apr 7;132(13):4506-7
pubmed: 20225875
J Am Chem Soc. 2014 Apr 9;136(14):5257-60
pubmed: 24712922
J Am Chem Soc. 2006 Jul 12;128(27):8754-6
pubmed: 16819868
Nature. 2016 Aug 17;536(7616):322-5
pubmed: 27535536
Chem Rev. 2016 Sep 14;116(17):10075-166
pubmed: 27285582
Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11200-4
pubmed: 26212356
Angew Chem Int Ed Engl. 2011 Sep 19;50(39):9081-4
pubmed: 21748831
Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6828-38
pubmed: 22711502
Chem Soc Rev. 2017 Aug 29;46(17):5193-5203
pubmed: 28762417
Angew Chem Int Ed Engl. 2011 Mar 21;50(13):2990-4
pubmed: 21404384
Chem Rev. 2013 Jul 10;113(7):5322-63
pubmed: 23509883
Chem Rev. 2016 Jan 27;116(2):422-518
pubmed: 26756377
J Am Chem Soc. 2016 Mar 2;138(8):2520-3
pubmed: 26890498
Chem Soc Rev. 2008 Feb;37(2):320-30
pubmed: 18197348
J Am Chem Soc. 2009 Jun 10;131(22):7520-1
pubmed: 19435367
Chem Rev. 2015 Jan 28;115(2):931-72
pubmed: 25347593
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15632-41
pubmed: 26509837
Angew Chem Int Ed Engl. 2020 Dec 14;59(51):23056-23060
pubmed: 32896054
Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10034-10072
pubmed: 29457971
Nat Chem. 2018 Feb;10(2):205-211
pubmed: 29359756
Chem Sci. 2015 Dec 1;6(12):7206-7212
pubmed: 29861956

Auteurs

Xiang Sun (X)

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

Tobias Ritter (T)

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

Classifications MeSH