Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
29 01 2020
29 01 2020
Historique:
pubmed:
7
1
2020
medline:
20
1
2021
entrez:
7
1
2020
Statut:
ppublish
Résumé
The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.
Identifiants
pubmed: 31904939
doi: 10.1021/jacs.9b11472
pmc: PMC7251231
mid: NIHMS1581498
doi:
Substances chimiques
Cyclopropanes
0
Ethers
0
Carbon
7440-44-0
cyclopropene
7B8994OHJ0
Hydrogen
7YNJ3PO35Z
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
1698-1703Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM127135
Pays : United States
Références
Acc Chem Res. 2015 Nov 17;48(11):2895-903
pubmed: 26545103
Acc Chem Res. 2011 Jan 18;44(1):36-46
pubmed: 20977224
European J Org Chem. 2017 Apr 18;2017(15):2056-2071
pubmed: 30147436
Science. 2018 Aug 17;361(6403):668-672
pubmed: 30049785
Angew Chem Int Ed Engl. 2019 Mar 26;58(14):4592-4595
pubmed: 30650241
Nature. 2018 Aug;560(7716):70-75
pubmed: 30068953
J Med Chem. 2014 Jul 24;57(14):5845-59
pubmed: 24471928
Science. 2015 Sep 25;349(6255):1532-6
pubmed: 26316601
Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1565-9
pubmed: 25470570
Science. 2012 Feb 17;335(6070):807-9
pubmed: 22344434
Science. 2006 Apr 7;312(5770):67-72
pubmed: 16601184
Angew Chem Int Ed Engl. 2019 Sep 23;58(39):13666-13699
pubmed: 30888102
Angew Chem Int Ed Engl. 2019 May 6;58(19):6385-6390
pubmed: 30763466
J Org Chem. 2016 Dec 2;81(23):11743-11750
pubmed: 27787990
Chem Sci. 2017 May 1;8(5):4044-4050
pubmed: 30155212
Angew Chem Int Ed Engl. 2020 Jan 7;59(2):658-662
pubmed: 31583795
J Med Chem. 2019 Mar 14;62(5):2256-2264
pubmed: 30272973
Nature. 2015 Mar 5;519(7541):74-7
pubmed: 25739630
J Med Chem. 2011 May 26;54(10):3451-79
pubmed: 21504168
Nat Catal. 2019 Apr;2(4):266-373
pubmed: 30984910
Nature. 2015 Sep 3;525(7567):87-90
pubmed: 26308895
Synthesis (Stuttg). 2018 Apr;50(8):1569-1586
pubmed: 29755145
Angew Chem Int Ed Engl. 2019 Sep 16;58(38):13318-13322
pubmed: 31306561
Angew Chem Int Ed Engl. 2018 Jan 2;57(1):62-101
pubmed: 29206316
Nature. 2007 Mar 22;446(7134):391-3
pubmed: 17377575
Chem Rev. 2010 Feb 10;110(2):1147-69
pubmed: 20078038
Acc Chem Res. 2018 Nov 20;51(11):2628-2640
pubmed: 30406655
Org Biomol Chem. 2015 Dec 14;13(46):11341-50
pubmed: 26419479
J Am Chem Soc. 2010 Sep 29;132(38):13194-6
pubmed: 20812741
J Org Chem. 2017 Oct 6;82(19):10704-10709
pubmed: 28862002
Chem Commun (Camb). 2016 Jan 25;52(7):1490-3
pubmed: 26660120
J Am Chem Soc. 2019 Feb 6;141(5):1882-1886
pubmed: 30669845