Arylazo Sulfones as Nonionic Visible-Light Photoacid Generators.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
19 May 2023
Historique:
medline: 23 7 2022
pubmed: 23 7 2022
entrez: 22 7 2022
Statut: ppublish

Résumé

The selective visible-light-driven generation of a weak acid (sulfinic acid, in nitrogen-purged solutions) or a strong acid (sulfonic acid, in oxygen-purged solutions) by using shelf-stable arylazo sulfones was developed. These sulfones were then used for the green, smooth, and efficient photochemical catalytic protection of several (substituted) alcohols (and phenols) as tetrahydropyranyl ethers or acetals.

Identifiants

pubmed: 35866712
doi: 10.1021/acs.joc.2c01248
pmc: PMC10204067
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

6313-6321

Références

Chemistry. 2022 May 6;28(26):e202200333
pubmed: 35319124
Langmuir. 2020 Mar 24;36(11):2786-2793
pubmed: 32090577
J Am Chem Soc. 2007 Nov 7;129(44):13378-9
pubmed: 17935334
J Am Chem Soc. 2020 Jun 10;142(23):10516-10525
pubmed: 32412759
Org Lett. 2016 Sep 16;18(18):4534-7
pubmed: 27602486
Org Lett. 2019 Nov 1;21(21):8528-8532
pubmed: 31638823
Acc Chem Res. 2017 Aug 15;50(8):1956-1964
pubmed: 28692282
J Org Chem. 2017 Aug 4;82(15):8040-8047
pubmed: 28686024
Org Lett. 2019 Jul 5;21(13):5187-5191
pubmed: 31247810
Molecules. 2019 Dec 30;25(1):
pubmed: 31905900
Org Lett. 2020 Aug 7;22(15):5844-5849
pubmed: 32678618
Photochem Photobiol Sci. 2022 May;21(5):687-694
pubmed: 34750786
J Org Chem. 2020 Oct 16;85(20):12813-12822
pubmed: 32956584
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10410-10422
pubmed: 30575230
Chemistry. 2016 Nov 14;22(47):16998-17005
pubmed: 27739113
Chem Commun (Camb). 2013 Oct 4;49(76):8480-2
pubmed: 23939219
Org Lett. 2020 Feb 7;22(3):1208-1212
pubmed: 31944778
Chem Res Toxicol. 2017 Jan 17;30(1):13-37
pubmed: 27617882
Chem Commun (Camb). 2007 Dec 14;(46):4928-30
pubmed: 18361372
Chemistry. 2008;14(30):9286-91
pubmed: 18780382
J Am Chem Soc. 2021 Dec 15;143(49):20758-20768
pubmed: 34846132
Org Biomol Chem. 2021 Jul 28;19(29):6487-6492
pubmed: 34241618
Chem Rev. 2004 Jan;104(1):199-250
pubmed: 14719975
J Am Chem Soc. 2018 Jul 5;140(26):8350-8356
pubmed: 29939024
Chem Asian J. 2019 Feb 1;14(3):438-445
pubmed: 30536732
J Org Chem. 2008 Jun 20;73(12):4743-5
pubmed: 18505291
J Org Chem. 2016 Oct 21;81(20):9612-9619
pubmed: 27696841
Org Lett. 2011 Apr 15;13(8):1932-5
pubmed: 21395228
J Am Chem Soc. 2011 Sep 21;133(37):14699-703
pubmed: 21823603
Acc Chem Res. 2002 Jan;35(1):19-27
pubmed: 11790085

Auteurs

Lorenzo Di Terlizzi (L)

PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Angelo Martinelli (A)

Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Daniele Merli (D)

Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Stefano Protti (S)

PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Maurizio Fagnoni (M)

PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Classifications MeSH