Overcoming Limitations in Decarboxylative Arylation via Ag-Ni Electrocatalysis.
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:
28 09 2022
28 09 2022
Historique:
pubmed:
16
9
2022
medline:
30
9
2022
entrez:
15
9
2022
Statut:
ppublish
Résumé
A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag-Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined in a surprisingly simple way: open to the air, using technical-grade solvents, an inexpensive ligand and Ni source, and substoichiometric AgNO
Identifiants
pubmed: 36106767
doi: 10.1021/jacs.2c08006
pmc: PMC9805175
mid: NIHMS1860989
doi:
Substances chimiques
Esters
0
Ligands
0
Solvents
0
Types de publication
Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
17709-17720Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM118176
Pays : United States
Références
Eur J Med Chem. 2013 Aug;66:355-63
pubmed: 23816880
J Med Chem. 2014 Dec 26;57(24):10257-74
pubmed: 25255204
Science. 2019 Jan 25;363(6425):405-408
pubmed: 30679373
Org Biomol Chem. 2022 Mar 2;20(9):1969-1973
pubmed: 35175267
Chem Sci. 2017 Jan 1;8(1):530-535
pubmed: 28451200
Org Lett. 2004 Oct 28;6(22):4129-32
pubmed: 15496116
Science. 2015 Jan 2;347(6217):49-53
pubmed: 25554781
Org Lett. 2019 Feb 1;21(3):816-820
pubmed: 30673257
J Am Chem Soc. 2002 Nov 20;124(46):13856-63
pubmed: 12431116
J Org Chem. 2015 Aug 7;80(15):7642-51
pubmed: 26140623
Angew Chem Int Ed Engl. 2021 May 10;60(20):11068-11091
pubmed: 32940402
Science. 2022 Feb 18;375(6582):745-752
pubmed: 35175791
Acc Chem Res. 2018 Aug 21;51(8):1807-1817
pubmed: 30070821
Amino Acids. 2016 Sep;48(9):2243-51
pubmed: 27229336
ACS Med Chem Lett. 2020 Mar 23;11(4):597-604
pubmed: 32292569
Chem Sci. 2021 Mar 5;12(15):5450-5457
pubmed: 34168786
J Am Chem Soc. 2002 Dec 18;124(50):14844-5
pubmed: 12475315
J Med Chem. 2019 Mar 14;62(5):2256-2264
pubmed: 30272973
J Org Chem. 2017 Jul 21;82(14):7085-7092
pubmed: 28682073
Org Lett. 2000 Apr 20;2(8):1089-92
pubmed: 10804561
Chem Sci. 2016 Apr 21;7(4):2604-2613
pubmed: 28660032
Chemistry. 2020 Mar 12;26(15):3226-3230
pubmed: 31804733
Synlett. 2014 Jan;25(2):233-238
pubmed: 24795502
Beilstein J Org Chem. 2013 Oct 30;9:2265-319
pubmed: 24204439
J Med Chem. 2014 Jul 10;57(13):5714-27
pubmed: 24918870
ACS Cent Sci. 2021 Aug 25;7(8):1347-1355
pubmed: 34471679
Chem Soc Rev. 2018 Oct 29;47(21):7851-7866
pubmed: 30101272
Acc Chem Res. 2021 Feb 2;54(3):605-617
pubmed: 33476518
J Am Chem Soc. 2010 Jan 27;132(3):920-1
pubmed: 20047282
Tetrahedron Lett. 2021 Aug 31;79:
pubmed: 34483378
Science. 2022 Apr 29;376(6592):532-539
pubmed: 35482871
Acc Chem Res. 2019 Oct 15;52(10):2858-2869
pubmed: 31573791
Chemistry. 2017 Jun 1;23(31):7382-7401
pubmed: 27859719
Angew Chem Int Ed Engl. 2019 Sep 23;58(39):13666-13699
pubmed: 30888102
J Org Chem. 2014 Sep 19;79(18):8871-6
pubmed: 25140886
J Am Chem Soc. 2016 Oct 5;138(39):12692-12714
pubmed: 27631602
Chemistry. 2021 Sep 9;27(51):12981-12986
pubmed: 34233043
J Am Chem Soc. 2016 Apr 20;138(15):5016-9
pubmed: 27029833
Med Res Rev. 2020 Mar;40(2):709-752
pubmed: 31512284
J Am Chem Soc. 2016 Feb 24;138(7):2174-7
pubmed: 26835704