N,N'-Ethylene-Bridged Bis-2-Aryl-Pyrrolinium Cations to E-Diaminoalkenes: Non-Identical Stepwise Reversible Double-Redox Coupled Bond Activation Reactions.
carbocations
electrochemistry
non-identical reversible reaction
radical reactions
redox chemistry
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Apr 2020
01 Apr 2020
Historique:
received:
16
01
2020
pubmed:
30
1
2020
medline:
30
1
2020
entrez:
30
1
2020
Statut:
ppublish
Résumé
This work presents a stepwise reversible two-electron transfer induced hydrogen shift leading to the conversion of a bis-pyrrolinium cation to an E-diaminoalkene and vice versa. Remarkably, the forward and the reverse reaction, which are both reversible, follow two completely different reaction pathways. Establishing such unprecedented property in this type of processes was possible by developing a novel synthetic route towards the starting dication. All intermediates involved in both the forward and the backward reactions were comprehensively characterized by a combination of spectroscopic, crystallographic, electrochemical, spectroelectrochemical, and theoretical methods. The presented synthetic route opens up new possibilities for the generation of multi-pyrrolinium cation scaffold-based organic redox systems, which constitute decidedly sought-after molecules in contemporary chemistry.
Identifiants
pubmed: 31994763
doi: 10.1002/chem.202000255
pmc: PMC7187269
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4425-4431Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
J Am Chem Soc. 2015 Jun 17;137(23):7519-25
pubmed: 26011769
Chemistry. 2020 Apr 1;26(19):4425-4431
pubmed: 31994763
Angew Chem Int Ed Engl. 2013 Feb 4;52(6):1801-5
pubmed: 23280727
Nature. 1992 Feb 27;355(6363):796-802
pubmed: 1311417
Chem Commun (Camb). 2010 Jun 21;46(23):4100-2
pubmed: 20390155
Nature. 2010 Jan 14;463(7278):171-7
pubmed: 20075912
Angew Chem Int Ed Engl. 2004 Aug 6;43(31):4089-93
pubmed: 15300703
J Am Chem Soc. 2018 Feb 14;140(6):2206-2213
pubmed: 29342351
Angew Chem Int Ed Engl. 2017 Aug 14;56(34):10209-10213
pubmed: 28387046
Acc Chem Res. 2015 Feb 17;48(2):256-66
pubmed: 25515548
Proc Natl Acad Sci U S A. 2004 Nov 16;101(46):16198-203
pubmed: 15534221
Chemistry. 2001 Mar 16;7(6):1266-72
pubmed: 11322553
Angew Chem Int Ed Engl. 2012 Jan 9;51(2):326-92
pubmed: 22095940
Angew Chem Int Ed Engl. 2005 Sep 5;44(35):5705-9
pubmed: 16059961
J Am Chem Soc. 2013 Dec 18;135(50):18766-9
pubmed: 24304381
J Am Chem Soc. 2002 May 22;124(20):5702-13
pubmed: 12010043
Materials (Basel). 2011 Oct 26;4(11):1906-1926
pubmed: 28824114
Chem Rev. 2014 Jun 11;114(11):5848-958
pubmed: 24750169
Science. 1998 Mar 20;279(5358):1891-5
pubmed: 9506932
Org Lett. 2004 Jul 22;6(15):2523-6
pubmed: 15255681
Chem Rev. 2000 Jan 12;100(1):39-92
pubmed: 11749234
Chem Rev. 2012 Jul 11;112(7):4016-93
pubmed: 22702235
Chem Rev. 2003 Jan;103(1):229-82
pubmed: 12517185
Nat Chem. 2011 Feb;3(2):120-5
pubmed: 21258384
Chem Sci. 2019 Feb 28;10(14):4077-4081
pubmed: 31049189
J Am Chem Soc. 2018 Nov 7;140(44):14823-14835
pubmed: 30351018
Inorg Chem. 2018 Jan 2;57(1):435-445
pubmed: 29220166
Science. 2007 Apr 20;316(5823):439-41
pubmed: 17446400
J Am Chem Soc. 2004 Nov 17;126(45):14706-7
pubmed: 15535680
Angew Chem Int Ed Engl. 2006 Dec 4;45(47):8059-62
pubmed: 17089438
Acc Chem Res. 2018 Oct 16;51(10):2391-2399
pubmed: 30234963
Chem Rev. 2008 Jul;108(7):2113-44
pubmed: 18620364
Org Lett. 2014 Oct 17;16(20):5410-3
pubmed: 25285730
J Am Chem Soc. 2012 Apr 4;134(13):5954-64
pubmed: 22390470
Nature. 2013 Sep 5;501(7465):84-7
pubmed: 24005414
Acc Chem Res. 2016 Mar 15;49(3):357-69
pubmed: 26925983
J Am Chem Soc. 2019 Jun 19;141(24):9701-9711
pubmed: 31125215
Sci Rep. 2015 Dec 22;5:18446
pubmed: 26689792
Nat Chem. 2018 Dec;10(12):1196-1200
pubmed: 30323332
Science. 2012 Oct 5;338(6103):90-4
pubmed: 23042890
Science. 2019 Feb 1;363(6426):479-484
pubmed: 30705183
J Am Chem Soc. 2018 Feb 21;140(7):2546-2554
pubmed: 29382199
Chem Rev. 2018 Oct 10;118(19):9678-9842
pubmed: 29969239
Science. 2004 Mar 19;303(5665):1849-51
pubmed: 15031500
Chemistry. 2018 Aug 27;24(48):12722-12727
pubmed: 29797625
Org Lett. 2017 Oct 20;19(20):5605-5608
pubmed: 28968127
Phys Rev Lett. 2011 May 27;106(21):216103
pubmed: 21699320