title: Late-stage deoxyfluorination of alcohols with PhenoFluor.
abstract: An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.
authors: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
authors: Filippo
authors: F
authors: Sladojevich
authors: Sophie I
authors: SI
authors: Arlow
authors: Pingping
authors: P
authors: Tang
authors: Tobias
authors: T
authors: Ritter
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001665:Binding Sites; D054879:Halogenation; D048288:Imidazolines / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000438:Alcohols; D048288:Imidazolines; C583239:PhenoFluor
references: Org Lett. 2009 Nov 5;11(21):5050-3
references: 19799406
references: Nature. 2011 May 26;473(7348):470-7
references: 21614074
references: J Am Chem Soc. 2012 Apr 11;134(14):6120-3
references: 22462775
references: J Am Chem Soc. 2012 Oct 24;134(42):17456-8
references: 23061667
references: J Am Chem Soc. 2011 Aug 3;133(30):11482-4
references: 21736304
references: Chembiochem. 2004 May 3;5(5):637-43
references: 15122635
references: Nature. 2011 Dec 8;480(7376):224-8
references: 22158245
references: Angew Chem Int Ed Engl. 2012 Mar 19;51(12):2907-11
references: 22319027
references: Nat Prod Rep. 2008 Jun;25(3):475-516
references: 18497896
references: Angew Chem Int Ed Engl. 2006 Aug 25;45(34):5616-9
references: 16858713
references: J Am Chem Soc. 2012 Jun 13;134(23):9755-61
references: 22621706
references: Science. 2009 Sep 25;325(5948):1661-4
references: 19679769
references: J Am Chem Soc. 2010 Sep 1;132(34):12150-4
references: 20695434
references: Chem Commun (Camb). 2002 Aug 7;(15):1618-9
references: 12170810
references: J Am Chem Soc. 2009 Aug 26;131(33):11701-6
references: 19645492
references: J Nat Prod. 2007 Mar;70(3):461-77
references: 17309302
references: J Am Chem Soc. 2010 Dec 29;132(51):18199-205
references: 21125999
references: Science. 2011 Nov 4;334(6056):639-42
references: 22053044
references: Nat Chem. 2011 Dec;3(12):969-73
references: 22213919
references: Nature. 2012 Dec 6;492(7427):95-9
references: 23201691
references: J Am Chem Soc. 2012 Jan 25;134(3):1494-7
references: 22229949
references: J Chem Soc Perkin 1. 1971;10:1920-2
references: 5103806
references: Nat Chem. 2012 Jul 08;4(8):629-35
references: 22824894
references: Chem Soc Rev. 2008 Feb;37(2):320-30
references: 18197348
references: Curr Opin Drug Discov Devel. 2008 Nov;11(6):803-19
references: 18946845
references: Science. 2007 Sep 28;317(5846):1881-6
references: 17901324
references: Proc Natl Acad Sci U S A. 2011 Aug 30;108(35):14411-5
references: 21844378