title: One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.
abstract: A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA.
authors.forename: Alexandra E
authors.initials: AE
authors.lastname: Strom
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D015040:Zirconium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000588:Amines; D009942:Organometallic Compounds; D015040:Zirconium
references.citation: J Am Chem Soc. 2012 Apr 18;134(15):6571-4
references.pmid: 22469028
references.citation: Angew Chem Int Ed Engl. 2009;48(42):7841-4
references.pmid: 19760689
references.citation: J Am Chem Soc. 2009 Feb 18;131(6):2116-8
references.pmid: 19173650
references.citation: Carbohydr Res. 2012 May 1;352:197-201
references.pmid: 22370177
references.citation: ChemMedChem. 2010 Jan;5(1):79-85
references.pmid: 19943277
references.citation: Angew Chem Int Ed Engl. 2012 Apr 16;51(16):3953-6
references.pmid: 22407928
references.citation: Chem Rev. 1998 Apr 2;98(2):675-704
references.pmid: 11848912
references.citation: J Am Chem Soc. 2004 Aug 18;126(32):9906-7
references.pmid: 15303849
references.citation: J Org Chem. 2007 Sep 28;72(20):7551-9
references.pmid: 17760460
references.citation: Angew Chem Int Ed Engl. 2012 Apr 10;51(15):3642-5
references.pmid: 22383299
references.citation: J Am Chem Soc. 2012 Oct 10;134(40):16449-51
references.pmid: 23002712
references.citation: J Am Chem Soc. 2012 Nov 7;134(44):18253-6
references.pmid: 23082853
references.citation: Chem Rev. 2008 Sep;108(9):3795-892
references.pmid: 18729420