Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts.
alkylation
arylation
phosphane
phosphorus
photocatalysis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
09 Dec 2020
09 Dec 2020
Historique:
received:
01
06
2020
pubmed:
3
6
2020
medline:
3
6
2020
entrez:
3
6
2020
Statut:
ppublish
Résumé
Asymmetrically substituted tertiary phosphines and quaternary phosphonium salts are used extensively in applications throughout industry and academia. Despite their significance, classical methods to synthesize such compounds often demand either harsh reaction conditions, prefunctionalization of starting materials, highly sensitive organometallic reagents, or expensive transition-metal catalysts. Mild, practical methods thus remain elusive, despite being of great current interest. Herein, we describe a visible-light-driven method to form these products from secondary and primary phosphines. Using an inexpensive organic photocatalyst and blue-light irradiation, arylphosphines can be both alkylated and arylated using commercially available organohalides. In addition, the same organocatalyst can be used to transform white phosphorus (P
Identifiants
pubmed: 32484989
doi: 10.1002/chem.202002646
pmc: PMC7756875
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16374-16382Subventions
Organisme : H2020 European Research Council
ID : ERC CoG 772299
Organisme : Alexander von Humboldt-Stiftung
Organisme : Deutsche Forschungsgemeinschaft
ID : GRK 1626
Organisme : Deutsche Forschungsgemeinschaft
ID : FOR2177
Informations de copyright
2020 The Authors. Published by Wiley-VCH GmbH.
Références
ACS Appl Mater Interfaces. 2018 Feb 14;10(6):5569-5576
pubmed: 29359553
Dalton Trans. 2008 Jun 7;(21):2849-53
pubmed: 18478147
Org Biomol Chem. 2012 Jul 28;10(28):5327-31
pubmed: 22707074
Science. 2020 Feb 28;367(6481):1021-1026
pubmed: 32108109
Chem Commun (Camb). 2003 Dec 7;(23):2928-9
pubmed: 14680245
Chemistry. 2019 Sep 25;25(54):12502-12506
pubmed: 31339601
Nat Commun. 2016 Dec 01;7:13651
pubmed: 27905397
Chem Rev. 2018 Aug 22;118(16):7532-7585
pubmed: 30011194
Chemistry. 2016 Aug 26;22(36):12598-605
pubmed: 27405918
Dalton Trans. 2016 Dec 6;45(48):19172-19193
pubmed: 27891536
J Org Chem. 2008 Jan 18;73(2):590-3
pubmed: 18154356
Org Lett. 2010 Apr 2;12(7):1568-71
pubmed: 20222685
Chemistry. 2006 Dec 13;12(36):9314-22
pubmed: 17009361
Nat Catal. 2019 Dec;2(12):1101-1106
pubmed: 31844839
Inorg Chem. 2019 Apr 15;58(8):5325-5334
pubmed: 30933487
J Org Chem. 2003 May 30;68(11):4590-3
pubmed: 12762780
Beilstein J Org Chem. 2014 May 09;10:1064-96
pubmed: 24991257
Chemistry. 2013 Sep 27;19(40):13445-62
pubmed: 23955798
ACS Omega. 2019 Apr 11;4(4):6690-6696
pubmed: 31459795
Chem Soc Rev. 2013 Jan 7;42(1):97-113
pubmed: 22990664
Org Lett. 2003 Jun 26;5(13):2315-8
pubmed: 12816437
Org Lett. 2017 Nov 3;19(21):5786-5789
pubmed: 29039956
Chem Commun (Camb). 2013 Sep 7;49(69):7590-2
pubmed: 23873358
Org Lett. 2002 Mar 7;4(5):761-3
pubmed: 11869121
Chem Rev. 2003 May;103(5):1759-92
pubmed: 12744693
Chem Soc Rev. 2015 Apr 21;44(8):2508-28
pubmed: 25714261
Chem Rev. 2016 Sep 14;116(17):10075-166
pubmed: 27285582
Chem Commun (Camb). 2014 Oct 18;50(81):12109-11
pubmed: 25168587
J Org Chem. 2008 May 2;73(9):3530-4
pubmed: 18386908
Chemistry. 2020 Dec 9;26(69):16374-16382
pubmed: 32484989
ACS Appl Mater Interfaces. 2018 Oct 24;10(42):35896-35903
pubmed: 30260622
J Am Chem Soc. 2018 Nov 14;140(45):15353-15365
pubmed: 30277767
Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10034-10072
pubmed: 29457971
Chem Commun (Camb). 2016 Apr 11;52(28):4987-90
pubmed: 26898992