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Carboberyllation: addition of organoberyllium species to alkenes and alkynes. A comparison with carboboration

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Abstract

The potential for carbometallation reactions between organoberyllium and model alkenes and alkynes has been investigated in a computational study. Results indicate that barriers for carbometallation reactions between BeR2 and alkynes are as low as 100 kJ mol−1, and much lower than corresponding reactions with MgR2. In contrast to carboboration reactions with BR3, with organoberyllium 1,2-addition is favoured over 1,1-addition. It is concluded that carbometallation reactions with beryllium are likely feasible, and that the reaction between BePh2 and alkynes provides the best opportunity for the first experimental observation of carboberyllation.

Graphical abstract: Carboberyllation: addition of organoberyllium species to alkenes and alkynes. A comparison with carboboration

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Publication details

The article was received on 15 Apr 2017, accepted on 16 May 2017 and first published on 16 May 2017


Article type: Paper
DOI: 10.1039/C7DT01370A
Citation: Dalton Trans., 2017, Advance Article
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    Carboberyllation: addition of organoberyllium species to alkenes and alkynes. A comparison with carboboration

    T. E. Field-Theodore, S. A. Couchman, D. J. D. Wilson and J. L. Dutton, Dalton Trans., 2017, Advance Article , DOI: 10.1039/C7DT01370A

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