NHC-BIAN-Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
06 May 2022
06 May 2022
Historique:
pubmed:
9
4
2022
medline:
9
4
2022
entrez:
8
4
2022
Statut:
ppublish
Résumé
The direct catalytic alkynylation/dehydrative cyclization of 2-amino-3-trifluoroacetyl-pyridines on water was developed for the efficient synthesis of a broad range of fluorinated 1,8-naphthyridines from terminal alkynes. A novel N-heterocyclic carbene (NHC) ligand system that combines a π-extended acenaphthylene backbone with sterically bulky pentiptycene pendant groups was successfully utilized in a copper- or silver-mediated cyclization. Computational analysis of the reaction pathway supports our explanation of the different experimental conversions and yields for the set of copper and silver catalysts. The impact of steric hindrance at the metal center and the flexibility of substituents on the imidazole ring of the NHC on catalytic performance are also discussed.
Identifiants
pubmed: 35394784
doi: 10.1021/acs.joc.2c00380
pmc: PMC9087358
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6115-6136Références
Proc Natl Acad Sci U S A. 2010 Aug 24;107(34):14973-7
pubmed: 20689041
Chem Rev. 2014 Feb 26;114(4):2432-506
pubmed: 24299176
Org Lett. 2017 Aug 18;19(16):4163-4166
pubmed: 28753029
Pharmazie. 2007 Dec;62(12):919-24
pubmed: 18214343
Chem Rev. 2016 Jan 27;116(2):422-518
pubmed: 26756377
Acc Chem Res. 2016 Oct 18;49(10):2146-2157
pubmed: 27656765
Antimicrob Agents Chemother. 1996 Jun;40(6):1564-8
pubmed: 8726042
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11906-11910
pubmed: 28636185
J Am Chem Soc. 2019 Jul 24;141(29):11409-11413
pubmed: 31282153
Dalton Trans. 2017 Jan 17;46(3):614-627
pubmed: 27924321
Angew Chem Int Ed Engl. 2005 Mar 11;44(12):1840-3
pubmed: 15714454
Chem Commun (Camb). 2013 Nov 18;49(89):10483-5
pubmed: 24087835
Dalton Trans. 2020 Sep 22;49(36):12592-12598
pubmed: 32856673
J Am Chem Soc. 2005 Dec 28;127(51):18020-1
pubmed: 16366550
Chem Rev. 2015 Jan 28;115(2):612-33
pubmed: 25474722
J Am Chem Soc. 2005 Jan 26;127(3):810-1
pubmed: 15656599
Nat Chem. 2017 Nov;9(11):1105-1109
pubmed: 29064496
J Am Chem Soc. 2017 Apr 19;139(15):5378-5386
pubmed: 28394586
J Am Chem Soc. 2018 Apr 18;140(15):5161-5170
pubmed: 29617115
PLoS One. 2010 Apr 15;5(4):e10186
pubmed: 20419121
Arch Pharm (Weinheim). 2015 Dec;348(12):837-60
pubmed: 26548568
Steroids. 2012 Sep;77(11):1075-85
pubmed: 22613036
J Am Chem Soc. 2011 Jun 1;133(21):8138-41
pubmed: 21553862
J Org Chem. 2003 Dec 26;68(26):10178-80
pubmed: 14682721
Org Lett. 2017 Oct 20;19(20):5625-5628
pubmed: 29019411
Chem Rev. 2018 Oct 10;118(19):9457-9492
pubmed: 29601194
Chem Rev. 2016 Oct 12;116(19):11924-11966
pubmed: 27548659
Chemistry. 2010 Dec 27;16(48):14348-53
pubmed: 21082623
Chemistry. 2016 Jun 6;22(24):8089-94
pubmed: 27142642
Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10723-10727
pubmed: 29889348
Anticancer Agents Med Chem. 2012 Jul;12(6):653-62
pubmed: 22263796
Chem Rev. 2016 Jan 27;116(2):719-66
pubmed: 26751274
J Am Chem Soc. 2002 Jun 19;124(24):6810-1
pubmed: 12059186
Med Res Rev. 1996 Sep;16(5):433-86
pubmed: 8865150
J Med Chem. 2017 Jan 26;60(2):797-804
pubmed: 28051859
J Org Chem. 2017 Aug 4;82(15):7980-7997
pubmed: 28686022
Org Lett. 2016 Apr 15;18(8):1724-7
pubmed: 27018895
Org Biomol Chem. 2019 Mar 13;17(11):2839-2849
pubmed: 30672560
Org Lett. 2019 Nov 1;21(21):8805-8809
pubmed: 31626553
Chemistry. 2012 Apr 10;18(15):4517-21
pubmed: 22415936
Org Biomol Chem. 2016 Jun 28;14(24):5591-4
pubmed: 27030373
Dalton Trans. 2005 Jan 7;(1):37-43
pubmed: 15605145
J Am Chem Soc. 2007 Oct 3;129(39):11898-9
pubmed: 17850087
Chemistry. 2021 Mar 8;27(14):4478-4499
pubmed: 32989914
Dalton Trans. 2016 Jul 5;45(27):11015-24
pubmed: 27312675
Chemistry. 2010 Dec 27;16(48):14335-47
pubmed: 21077060
J Am Chem Soc. 2018 Feb 7;140(5):1576-1579
pubmed: 29211456
Bioorg Chem. 2018 Oct;80:245-252
pubmed: 29966870
J Med Chem. 2018 Jul 26;61(14):5822-5880
pubmed: 29400967
Chem Rev. 2015 Sep 9;115(17):9073-174
pubmed: 25854146
Science. 2019 Feb 22;363(6429):857-862
pubmed: 30792299
J Am Chem Soc. 2015 May 20;137(19):6168-71
pubmed: 25951226
Org Lett. 2015 Sep 18;17(18):4640-3
pubmed: 26335721
J Med Pharm Chem. 1962 Sep;91:1063-5
pubmed: 14056431
J Am Chem Soc. 2009 Jan 21;131(2):763-77
pubmed: 19093863
Chem Commun (Camb). 2015 Feb 4;51(10):1933-6
pubmed: 25531810
J Am Chem Soc. 2017 Aug 30;139(34):11686-11689
pubmed: 28806870
J Am Chem Soc. 2018 Mar 21;140(11):4110-4118
pubmed: 29488760
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8
pubmed: 25567568
Chem Commun (Camb). 2007 Mar 14;(10):1026-8
pubmed: 17325794
J Med Chem. 2019 Feb 14;62(3):1348-1361
pubmed: 30609350
Nat Chem. 2019 Oct;11(10):872-879
pubmed: 31477851
J Am Chem Soc. 2004 Mar 24;126(11):3559-66
pubmed: 15025485
Chem Commun (Camb). 2017 Jul 4;53(54):7545-7548
pubmed: 28634609
J Am Chem Soc. 2018 Jul 18;140(28):8662-8666
pubmed: 29956921
Chemistry. 2013 Jul 29;19(31):10370-7
pubmed: 23788404
Nat Chem. 2020 Feb;12(2):180-185
pubmed: 31959960
Chem Commun (Camb). 2014 Dec 11;50(95):14926-37
pubmed: 25155373
Antimicrob Agents Chemother. 1996 Dec;40(12):2691-7
pubmed: 9124824
Dalton Trans. 2013 May 28;42(20):7312-7
pubmed: 23235534
Chem Soc Rev. 2008 Feb;37(2):320-30
pubmed: 18197348
J Enzyme Inhib Med Chem. 2016 Dec;31(6):974-82
pubmed: 26308114
Chem Rev. 2009 Jun;109(6):2652-71
pubmed: 19361199
Angew Chem Int Ed Engl. 2021 May 10;60(20):11068-11091
pubmed: 32940402
J Am Chem Soc. 2017 Oct 4;139(39):13672-13675
pubmed: 28918626
J Nat Prod. 2010 Oct 22;73(10):1727-9
pubmed: 20836516
J Am Chem Soc. 2011 Apr 27;133(16):6371-9
pubmed: 21469644
Eur J Med Chem. 2019 Feb 15;164:121-170
pubmed: 30594028
Leukemia. 2011 Dec;25(12):1808-14
pubmed: 21760592
Catal Sci Technol. 2021 May 7;11(9):3189-3197
pubmed: 34211698
J Am Chem Soc. 2010 Mar 31;132(12):4249-58
pubmed: 20205432
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):9948-53
pubmed: 26119321