Carboberyllation: addition of organoberyllium species to alkenes and alkynes. A comparison with carboborationElectronic supplementary information (ESI) available: Cartesian coordinates of optimized geometries, figures of optimized geometries. See DOI: 10.1039/c7dt01370a

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 BeR 2 and alkynes are as low as 100 kJ mol −1 , and much lower than corresponding reactions with MgR 2 . In contrast to carboboration reactions with BR 3 , 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 BePh 2 and alkynes provides the best opportunity for the first experimental observation of carboberyllation. A theoretical evaluation of the unknown addition of diorganoberyllium to model alkenes and alkynes (carboberyllation) shows the reaction with alkynes should be feasible. In contrast with carboboration a 1,2-regioselectivity is predicted.