Stereospecific and Chemoselective Copper-Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates.

copper nucleophilic substitution silanes stereospecificity transmetalation

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:
20 Jan 2020
Historique:
received: 30 09 2019
pubmed: 16 11 2019
medline: 16 11 2019
entrez: 16 11 2019
Statut: ppublish

Résumé

A method for the synthesis of benzylsilanes starting from the corresponding ammonium triflates is reported. Silyl boronic esters are employed as silicon pronucleophiles, and the reaction is catalyzed by copper(I) salts. Enantioenriched benzylic ammonium salts react stereospecifically through an S

Identifiants

pubmed: 31730248
doi: 10.1002/anie.201912490
pmc: PMC7003868
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

1577-1580

Subventions

Organisme : Deutsche Forschungsgemeinschaft
ID : Oe 249/15-1
Organisme : Einstein Stiftung Berlin

Informations de copyright

© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Références

Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3571-3574
pubmed: 30650228
J Am Chem Soc. 2016 May 25;138(20):6404-7
pubmed: 27187869
J Am Chem Soc. 2016 Nov 2;138(43):14222-14225
pubmed: 27744687
J Am Chem Soc. 2018 Apr 18;140(15):5014-5017
pubmed: 29589919
Chem Rev. 2019 Jul 10;119(13):8192-8228
pubmed: 31184483
Chem Commun (Camb). 2012 Aug 18;48(64):8006-8
pubmed: 22772394
Chem Commun (Camb). 2016 Apr 25;52(32):5609-12
pubmed: 27026113
Org Lett. 2011 Aug 19;13(16):4462-5
pubmed: 21786824
Tetrahedron. 2014 Jul 8;70(27-28):4257-4263
pubmed: 25364060
Org Lett. 2017 Dec 15;19(24):6562-6565
pubmed: 29192788
Chem Rev. 2013 Jan 9;113(1):402-41
pubmed: 23163551
Org Lett. 2016 Jan 4;18(1):136-9
pubmed: 26679212
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3575-3578
pubmed: 30644631
Chem Commun (Camb). 2018 Jul 24;54(60):8343-8346
pubmed: 29992220
Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1577-1580
pubmed: 31730248
Chem Sci. 2015 May 1;6(5):2943-2951
pubmed: 29308171
Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14529-14532
pubmed: 30079625
Chemistry. 2010 Jan 11;16(2):402-12
pubmed: 19937624
Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11649-11652
pubmed: 28742250
J Am Chem Soc. 2017 Jun 14;139(23):7741-7744
pubmed: 28570065
Angew Chem Int Ed Engl. 2019 Aug 5;58(32):11112-11117
pubmed: 31168946
J Am Chem Soc. 2017 Jun 28;139(25):8448-8451
pubmed: 28613864
ACS Catal. 2017 Dec 1;7(12):8113-8117
pubmed: 29868244
J Am Chem Soc. 2013 Jan 9;135(1):280-5
pubmed: 23268734
Chem Commun (Camb). 2012 Nov 11;48(87):10751-3
pubmed: 23010655
Chem Rev. 2015 Nov 11;115(21):12045-90
pubmed: 26423200
Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12141-12145
pubmed: 30070420
J Am Chem Soc. 2017 Jul 19;139(28):9439-9442
pubmed: 28654260

Auteurs

Jonas Scharfbier (J)

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.

Benjamin M Gross (BM)

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.

Martin Oestreich (M)

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.

Classifications MeSH