Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines.


Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
20 08 2021
Historique:
pubmed: 31 7 2021
medline: 31 7 2021
entrez: 30 7 2021
Statut: ppublish

Résumé

A nickel-catalyzed deaminative cyanation of Katritzky pyridinium salts has been developed. When it is coupled with formation of the pyridinium salt from primary amines, this method enables alkyl amines to be converted to alkyl nitriles. A less toxic cyanide reagent, Zn(CN)

Identifiants

pubmed: 34328332
doi: 10.1021/acs.orglett.1c01959
pmc: PMC8653511
mid: NIHMS1754368
doi:

Types de publication

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

Langues

eng

Sous-ensembles de citation

IM

Pagination

6242-6245

Subventions

Organisme : NIH HHS
ID : S10 OD016267
Pays : United States
Organisme : NIGMS NIH HHS
ID : T32 GM133395
Pays : United States
Organisme : NIGMS NIH HHS
ID : P20 GM103541
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM131816
Pays : United States
Organisme : NIGMS NIH HHS
ID : P20 GM104316
Pays : United States

Références

Mol Cancer Ther. 2014 Jul;13(7):1690-703
pubmed: 24688051
J Med Chem. 2020 Aug 13;63(15):8408-8418
pubmed: 32663408
J Am Chem Soc. 2019 Feb 13;141(6):2257-2262
pubmed: 30682254
J Am Chem Soc. 2015 Nov 4;137(43):13902-7
pubmed: 26491957
Org Lett. 2018 Dec 7;20(23):7735-7739
pubmed: 30431281
Adv Pharmacol. 2010;58:19-62
pubmed: 20655477
Chem Pharm Bull (Tokyo). 1995 Apr;43(4):699-702
pubmed: 7600620
J Am Chem Soc. 2019 Oct 16;141(41):16197-16201
pubmed: 31565935
Prog Med Chem. 2002;40:1-22
pubmed: 12516521
Front Psychol. 2015 Oct 06;6:1520
pubmed: 26500584
J Med Chem. 2010 Nov 25;53(22):7902-17
pubmed: 20804202
Lancet. 2012 Mar 10;379(9819):867
pubmed: 22405249
Org Lett. 2018 May 18;20(10):3030-3033
pubmed: 29745674
J Mater Chem B. 2016 Apr 7;4(13):2359-2368
pubmed: 32263231
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
Chem Rev. 2016 Oct 12;116(19):12564-12649
pubmed: 27689804
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12336-12339
pubmed: 28762257
J Am Chem Soc. 2019 Jan 30;141(4):1788-1796
pubmed: 30612428
Chem Soc Rev. 2011 Oct;40(10):5049-67
pubmed: 21528150
J Am Chem Soc. 2017 Apr 19;139(15):5313-5316
pubmed: 28359153
J Pharmacol Exp Ther. 2003 Sep;306(3):954-64
pubmed: 12750432
Org Lett. 2019 Apr 19;21(8):2947-2951
pubmed: 30924663
Org Lett. 2019 Apr 19;21(8):2941-2946
pubmed: 30917282

Auteurs

Jianyu Xu (J)

Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

J Cameron Twitty (JC)

Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

Mary P Watson (MP)

Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

Classifications MeSH