title: A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuR(F)].
abstract: A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuR(F)]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF(3)] is now commercially available and has been prepared on 20 g scale.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.
authors.forename: Nichole D
authors.initials: ND
authors.lastname: Litvinas
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Fier
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001965:Bromides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D054879:Halogenation; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000473:Alkanes; D001897:Boronic Acids; D001965:Bromides; D006841:Hydrocarbons, Aromatic; D003300:Copper
references.citation: J Org Chem. 2011 Feb 18;76(4):1174-6
references.pmid: 21235259
references.citation: Nature. 2011 May 26;473(7348):470-7
references.pmid: 21614074
references.citation: J Am Chem Soc. 2010 Mar 24;132(11):3648-9
references.pmid: 20184319
references.citation: Chem Rev. 2010 Feb 10;110(2):890-931
references.pmid: 20028025
references.citation: Angew Chem Int Ed Engl. 2011 Aug 8;50(33):7655-9
references.pmid: 21698725
references.citation: J Am Chem Soc. 2011 Jun 22;133(24):9286-9
references.pmid: 21627068
references.citation: Science. 2010 Jun 25;328(5986):1679-81
references.pmid: 20576888
references.citation: J Am Chem Soc. 2008 Jul 9;130(27):8600-1
references.pmid: 18543912
references.citation: Chem Rev. 2011 Aug 10;111(8):4475-521
references.pmid: 21456523
references.citation: J Am Chem Soc. 2005 Oct 19;127(41):14263-78
references.pmid: 16218621
references.citation: J Am Chem Soc. 2002 Jan 23;124(3):390-1
references.pmid: 11792205
references.citation: Org Lett. 2011 May 6;13(9):2342-5
references.pmid: 21473568
references.citation: Science. 2000 Mar 17;287(5460):1995-7
references.pmid: 10720320
references.citation: Chem Commun (Camb). 2009 Apr 14;(14):1909-11
references.pmid: 19319442
references.citation: Chem Commun (Camb). 2011 Jul 7;47(25):7236-8
references.pmid: 21614374
references.citation: Chem Commun (Camb). 2011 Apr 14;47(14):4300-2
references.pmid: 21380454
references.citation: Chemistry. 2011 Feb 25;17(9):2689-97
references.pmid: 21274956
references.citation: Org Lett. 2011 May 20;13(10):2548-51
references.pmid: 21513298
references.citation: Chem Soc Rev. 2008 Feb;37(2):320-30
references.pmid: 18197348
references.citation: Angew Chem Int Ed Engl. 2011 Apr 11;50(16):3793-8
references.pmid: 21442711
references.citation: Org Lett. 2010 Nov 5;12(21):5060-3
references.pmid: 20923196
references.citation: Science. 2007 Sep 28;317(5846):1881-6
references.pmid: 17901324
references.citation: Proc Natl Acad Sci U S A. 2011 Aug 30;108(35):14411-5
references.pmid: 21844378