N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.
N-heterocyclic carbenes
acid fluorides
organocatalysis
photochemistry
photoenolization
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:
17 Feb 2020
17 Feb 2020
Historique:
received:
12
11
2019
pubmed:
10
12
2019
medline:
10
12
2019
entrez:
10
12
2019
Statut:
ppublish
Résumé
The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits "ketone-like" photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels-Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.
Identifiants
pubmed: 31814280
doi: 10.1002/anie.201914456
pmc: PMC7027522
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3190-3194Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 420535461
Organisme : Deutsche Forschungsgemeinschaft
ID : 393271229
Organisme : Deutsche Forschungsgemeinschaft
ID : GRK 1582
Organisme : Verband der Chemischen Industrie
ID : Sachkostenzuschuss
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Nat Commun. 2017 May 25;8:15598
pubmed: 28541276
Synthesis (Stuttg). 2017 Jan;49(2):293-298
pubmed: 28690345
Chem Rev. 2015 Sep 9;115(17):9307-87
pubmed: 25992594
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):5941-5945
pubmed: 30843323
Chem Rev. 2007 Dec;107(12):5606-55
pubmed: 17956132
J Am Chem Soc. 2015 Aug 19;137(32):10112-5
pubmed: 26256839
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4712-4716
pubmed: 29380549
Org Biomol Chem. 2016 Oct 7;14(37):8641-7
pubmed: 27517138
J Am Chem Soc. 2019 Mar 6;141(9):3854-3858
pubmed: 30785739
Chem Rev. 2016 Sep 14;116(17):10035-74
pubmed: 27109441
Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12097-12101
pubmed: 30016564
Org Lett. 2017 May 5;19(9):2322-2325
pubmed: 28445064
Angew Chem Int Ed Engl. 2015 Mar 23;54(13):3872-90
pubmed: 25728854
Chem Sci. 2013 Aug 1;4(8):3020-3030
pubmed: 23878717
J Am Chem Soc. 2015 Feb 25;137(7):2416-9
pubmed: 25651161
Org Lett. 2014 Nov 7;16(21):5678-81
pubmed: 25343564
J Am Chem Soc. 2019 Sep 11;141(36):14073-14077
pubmed: 31449757
Org Lett. 2017 Sep 1;19(17):4452-4455
pubmed: 28799765
Angew Chem Int Ed Engl. 2020 Feb 17;59(8):3190-3194
pubmed: 31814280
Org Lett. 2018 Jan 19;20(2):333-336
pubmed: 29286252
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11875-11879
pubmed: 28746742
J Am Chem Soc. 2012 May 16;134(19):8094-7
pubmed: 22548244
J Am Chem Soc. 2013 Dec 18;135(50):18766-9
pubmed: 24304381
Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1000-45
pubmed: 21246702
Org Lett. 2015 Apr 17;17(8):1866-9
pubmed: 25822156
Chemistry. 2014 Apr 1;20(14):3874-86
pubmed: 24596102
Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3313-7
pubmed: 26797768
Photochem Photobiol Sci. 2019 Oct 9;18(10):2297-2362
pubmed: 31273370
Chem Soc Rev. 2018 Oct 29;47(21):7926-7953
pubmed: 29993045
J Am Chem Soc. 2009 Oct 14;131(40):14176-7
pubmed: 19757788
Nature. 2014 Jun 26;510(7506):485-96
pubmed: 24965649
Angew Chem Int Ed Engl. 2016 Dec 19;55(51):15783-15786
pubmed: 27873395
Nature. 2018 Jan 31;554(7690):41-49
pubmed: 29388950
Chem Rev. 2016 Sep 14;116(17):9850-913
pubmed: 27070820
Angew Chem Int Ed Engl. 2012 Nov 19;51(47):11686-98
pubmed: 23074146
J Am Chem Soc. 2014 Oct 22;136(42):14674-7
pubmed: 25302860
J Am Chem Soc. 2015 Nov 11;137(44):14063-6
pubmed: 26501185
Angew Chem Int Ed Engl. 2017 Mar 6;56(11):2942-2946
pubmed: 28151571
Chem Soc Rev. 2013 Jun 21;42(12):4906-17
pubmed: 23403488
Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11134-7
pubmed: 24038663
Adv Synth Catal. 2012 Jun 18;354(9):1617-1639
pubmed: 23538785
Org Biomol Chem. 2016 Aug 21;14(31):7392-442
pubmed: 27381273
Angew Chem Int Ed Engl. 2017 Mar 13;56(12):3304-3308
pubmed: 28185401
Chem Sci. 2015 Oct 1;6(10):6013-6018
pubmed: 29449915
Acc Chem Res. 2001 Jul;34(7):523-33
pubmed: 11456470
Angew Chem Int Ed Engl. 2018 Apr 3;57(15):3862-3873
pubmed: 29136320
Chem Rev. 2016 Sep 14;116(17):9683-747
pubmed: 27120289
Org Lett. 2016 Sep 2;18(17):4444-7
pubmed: 27549614