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Issue 3, 2012
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Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds

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Abstract

High nucleophilic reactivity and functional group tolerance are opposing properties of organometallic compounds. While organolithium compounds are highly nucleophilic and, therefore, react with most electrophiles, organosilicon compounds are on the low-reactivity end of the nucleophilicity scale. They tolerate numerous electrophilic functional groups and often require (Lewis) base activation in order to react. Organoboron compounds, which are key intermediates in organic synthesis, are positioned in between. While some of them undergo non-catalysed C–C bond forming reactions with various electrophiles, others tolerate a variety of functional groups and are most valuable substrates for Pd-catalysed cross-couplings (Suzuki–Miyaura reactions). As it is difficult for the preparative chemist to decide which functional groups are tolerated and which do react with organoboron reagents in the absence of a catalyst, we established a quantitative reactivity scale for representatives of the most important classes of organoboron reagents and we applied these data for predicting the feasibility of transition metal-free C–C bond forming reactions.

Graphical abstract: Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds

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Publication details

The article was received on 04 Nov 2011, accepted on 06 Dec 2011 and first published on 07 Dec 2011


Article type: Edge Article
DOI: 10.1039/C2SC00883A
Citation: Chem. Sci., 2012,3, 878-882
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    Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds

    G. Berionni, B. Maji, P. Knochel and H. Mayr, Chem. Sci., 2012, 3, 878
    DOI: 10.1039/C2SC00883A

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