Complementary Base Lowers the Barrier in SuFEx Click Chemistry for Primary Amine Nucleophiles.


Journal

ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658

Informations de publication

Date de publication:
08 Dec 2020
Historique:
received: 16 10 2020
accepted: 27 10 2020
entrez: 16 12 2020
pubmed: 17 12 2020
medline: 17 12 2020
Statut: epublish

Résumé

The sulfur(VI) fluoride exchange (SuFEx) reaction is an emerging scheme for connecting molecular building blocks. Due to its broad functional group tolerance and rather stable resulting linkage, it is seeing rapid adoption in various fields of chemistry. Still, to date the reaction mechanism is poorly understood, which hampers further development. Here, we show that the mechanism of the SuFEx reaction for the prototypical example of methanesulfonyl fluoride reacting with methylamine can be understood as an S

Identifiants

pubmed: 33324855
doi: 10.1021/acsomega.0c05049
pmc: PMC7726939
doi:

Types de publication

Journal Article

Langues

eng

Pagination

31432-31439

Informations de copyright

© 2020 American Chemical Society.

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

Références

J Am Chem Soc. 2018 Feb 28;140(8):2919-2925
pubmed: 29451783
Angew Chem Int Ed Engl. 2020 May 4;59(19):7494-7500
pubmed: 32157791
J Phys Chem Lett. 2018 Feb 15;9(4):768-772
pubmed: 29364670
Chemphyschem. 2018 Sep 25;:
pubmed: 30253016
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15150-15154
pubmed: 28914473
J Chem Theory Comput. 2009 Apr 14;5(4):962-75
pubmed: 26609605
J Phys Chem A. 2008 Apr 24;112(16):3722-30
pubmed: 18341310
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
Phys Chem Chem Phys. 2014 Jul 28;16(28):14489-95
pubmed: 24618654
Org Lett. 2020 Jun 5;22(11):4389-4394
pubmed: 32459499
J Mater Chem B. 2020 Jul 1;8(25):5529-5534
pubmed: 32494793
Chem Commun (Camb). 2020 Jul 21;56(58):8075-8078
pubmed: 32542267
ACS Comb Sci. 2014 Apr 14;16(4):192-7
pubmed: 24588358
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9430-48
pubmed: 25112519
J Am Chem Soc. 2005 Jan 12;127(1):210-6
pubmed: 15631470
Annu Rev Phys Chem. 1999;50:413-41
pubmed: 15012418
Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2004-2021
pubmed: 11433435
J Comput Chem. 2003 Jul 15;24(9):1142-56
pubmed: 12759913
ACS Appl Mater Interfaces. 2018 Oct 10;10(40):33785-33789
pubmed: 30230813
Inorg Chem. 2015 Jul 6;54(13):6363-72
pubmed: 26098713
Nat Chem. 2017 Nov;9(11):1083-1088
pubmed: 29064495
J Comput Chem. 2011 May;32(7):1456-65
pubmed: 21370243
Phys Chem Chem Phys. 2005 Sep 21;7(18):3297-305
pubmed: 16240044
Chemistry. 2018 Jul 20;24(41):10550-10556
pubmed: 29949211
J Am Chem Soc. 2018 Apr 18;140(15):4995-4999
pubmed: 29601199
Phys Rev Lett. 1996 Oct 28;77(18):3865-3868
pubmed: 10062328
Chempluschem. 2018 May;83(5):407-413
pubmed: 31957370
J Am Chem Soc. 2004 Jul 28;126(29):9054-8
pubmed: 15264838
Chemistry. 2020 Oct 1;26(55):12533-12538
pubmed: 32428384
Chemistry. 2017 Apr 24;23(23):5459-5466
pubmed: 28117524
Angew Chem Int Ed Engl. 2019 Mar 26;58(14):4552-4556
pubmed: 30740848
Org Lett. 2008 Apr 17;10(8):1633-6
pubmed: 18363405
Chem Soc Rev. 2019 Aug 27;48(17):4731-4758
pubmed: 31364998

Auteurs

Jan-Niclas Luy (JN)

Institut für Physikalische und Theoretische Chemie, Fakultät für Chemie und Pharmazie, Universität Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany.

Ralf Tonner (R)

Institut für Physikalische und Theoretische Chemie, Fakultät für Chemie und Pharmazie, Universität Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany.

Classifications MeSH