Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer.

Giese reactions deamination electron donor-acceptor complexes photochemistry radical reactions

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:
16 04 2019
Historique:
received: 02 01 2019
pubmed: 23 2 2019
medline: 23 2 2019
entrez: 23 2 2019
Statut: ppublish

Résumé

The use of pyridinium-activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst-free conditions is described. By taking advantage of the visible light absorptivity of electron donor-acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et

Identifiants

pubmed: 30794331
doi: 10.1002/anie.201814452
pmc: PMC6492299
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

5697-5701

Subventions

Organisme : Overseas Scholarship Program of Shaanxi Normal University
Pays : International
Organisme : H2020 European Research Council
ID : 670668
Pays : International
Organisme : The Fundamental Research Funds for the Central Universities (CN)
ID : GK201603034
Pays : International
Organisme : Engineering and Physical Sciences Research Council
ID : EP/I038071/1
Pays : International
Organisme : University of Auckland Doctoral Scholarship
Pays : International
Organisme : Engineering and Physical Sciences Research Council
ID : EP/R004978/1
Pays : International
Organisme : Biotechnology and Biological Sciences Research Council
ID : BB/F011539/1
Pays : United Kingdom

Informations de copyright

© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Références

Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1485-9
pubmed: 25475488
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4747-4751
pubmed: 29476596
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12336-12339
pubmed: 28762257
J Am Chem Soc. 2013 Aug 7;135(31):11521-4
pubmed: 23869694
Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1000-45
pubmed: 21246702
Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12819-12823
pubmed: 30098097
Chemistry. 2018 Nov 22;24(65):17210-17214
pubmed: 30290050
Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4447-4451
pubmed: 28323367
J Am Chem Soc. 2017 Apr 26;139(16):5736-5739
pubmed: 28402109
Chem Rev. 2008 Mar;108(3):1052-103
pubmed: 18302419
Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15227-15231
pubmed: 30253022
Nat Chem. 2017 Sep;9(9):868-873
pubmed: 28837165
J Am Chem Soc. 2015 May 6;137(17):5678-81
pubmed: 25901659
Nat Chem. 2013 Sep;5(9):750-6
pubmed: 23965676
Chem Rev. 2016 Sep 14;116(17):10035-74
pubmed: 27109441
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15039-15043
pubmed: 28984403
J Am Chem Soc. 2016 Jun 29;138(25):8019-30
pubmed: 27267587
Angew Chem Int Ed Engl. 2019 Apr 16;58(17):5697-5701
pubmed: 30794331
J Am Chem Soc. 2018 Aug 29;140(34):10700-10704
pubmed: 30091912
Photochem Photobiol Sci. 2009 Nov;8(11):1499-516
pubmed: 19862408
Angew Chem Int Ed Engl. 2011 Jun 27;50(27):6119-22
pubmed: 21604347
Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14017-21
pubmed: 26412046
Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12619-12623
pubmed: 28809077
Science. 2017 Jul 21;357(6348):283-286
pubmed: 28619717
Org Lett. 2018 Apr 6;20(7):2051-2054
pubmed: 29561620
J Org Chem. 2016 Aug 19;81(16):6898-926
pubmed: 27477076
Org Lett. 2017 Nov 3;19(21):5976-5979
pubmed: 29064719
Angew Chem Int Ed Engl. 2014 May 5;53(19):4921-5
pubmed: 24668827
Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9527-9531
pubmed: 28636809
Synthesis (Stuttg). 2018 Aug;50(16):3231-3237
pubmed: 30174353
J Org Chem. 2015 Jun 19;80(12):6025-36
pubmed: 26030520
Angew Chem Int Ed Engl. 2016 May 23;55(22):6515-9
pubmed: 27086646
Nature. 2018 Jan 31;554(7690):41-49
pubmed: 29388950
Chem Commun (Camb). 2018 Nov 8;54(90):12710-12713
pubmed: 30345997
J Am Chem Soc. 2017 Apr 19;139(15):5313-5316
pubmed: 28359153
Org Lett. 2016 Jun 17;18(12):2962-5
pubmed: 27227431
Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3730-3747
pubmed: 30339746
Chemistry. 2003 Feb 17;9(4):871-80
pubmed: 12584702
Nat Commun. 2018 Aug 16;9(1):3274
pubmed: 30115906
Chem Rev. 2016 Sep 14;116(17):10075-166
pubmed: 27285582
J Org Chem. 2015 Jun 19;80(12):6012-24
pubmed: 26030387
Acc Chem Res. 2008 May;41(5):641-53
pubmed: 18380446
Org Lett. 2018 Jun 1;20(11):3296-3299
pubmed: 29767989
Angew Chem Int Ed Engl. 2019 Jan 21;58(4):1213-1217
pubmed: 30419156
Nat Chem. 2010 Jul;2(7):527-32
pubmed: 20571569
J Am Chem Soc. 2017 Oct 4;139(39):13616-13619
pubmed: 28910097
J Am Chem Soc. 2015 May 20;137(19):6120-3
pubmed: 25748069
J Org Chem. 2012 Feb 17;77(4):1617-22
pubmed: 22283525
Org Lett. 2018 May 18;20(10):3030-3033
pubmed: 29745674
Chem. 2016 Sep 8;1(3):456-472
pubmed: 28462396

Auteurs

Jingjing Wu (J)

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Phillip S Grant (PS)

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Xiabing Li (X)

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Adam Noble (A)

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Varinder K Aggarwal (VK)

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Classifications MeSH