Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature

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Abstract

A commercially available 1,2-diamine serves as an effective ligand for metal-catalyzed cross-couplings of unactivated alkyl electrophiles at room temperature. In particular, Ni/trans-N,N‘-dimethyl-1,2-cyclohexanediamine provides the first method for achieving alkyl−alkyl Suzuki reactions of unactivated secondary alkyl halides with alkylboranes; earlier success in Suzuki couplings of such electrophiles had been restricted to reactions with aryl- and vinylboron reagents at elevated temperature.

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This article has been cited by 21 ACS Journal articles (5 most recent appear below).

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Stereochemistry of Transmetalation of Alkylboranes in Nickel-Catalyzed Alkyl–Alkyl Cross-Coupling Reactions

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  The Journal of Organic Chemistry2011 Article ASAP

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    Deuterium-labeled alkylborane reagents 2a and 2b were prepared and subjected to cross-coupling reactions in the presence of a nickel catalyst. NMR analysis of the products indicates that transmetalation from boron to nickel proceeds with retention of ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

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• 

  Diboration of Dialkynes with [2]Boraferrocenophanes

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    A series of new [4]diboradicarbametalloarenophanes was synthesized via transition-metal-mediated diboration of selected dialkynes by [Fe{η5-C5H4B(NMe2)}2] (3) and [Fe{η5-C5H4B(NMe2)}2Pt(PEt3)2] (18), respectively. Hereby, we have found three different ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides

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  Journal of the American Chemical Society2011 133 (18), 7084-7095

  • A Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides

    Peng Ren, Oleg Vechorkin, Kim von Allmen, Rosario Scopelliti, and Xile Hu
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    A structure–activity study was carried out for Ni catalyzed alkyl–alkyl Kumada-type cross coupling reactions. A series of new nickel(II) complexes including those with tridentate pincer bis(amino)amide ligands (RN2N) and those with bidentate mixed amino-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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