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

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 and alkynes are as low as 100 kJ mol , and much lower than corresponding reacti...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2017-06, Vol.46 (24), p.7686-7692
Main Authors: Field-Theodore, Terri E, Couchman, Shannon A, Wilson, David J D, Dutton, Jason L
Format: Article
Language:English
Subjects:
Alkenes
Alkynes
Barriers
Beryllium
Computation
Feasibility
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Summary: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 and alkynes are as low as 100 kJ mol , and much lower than corresponding reactions with MgR . In contrast to carboboration reactions with BR , 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 and alkynes provides the best opportunity for the first experimental observation of carboberyllation.
ISSN:1477-9226
1477-9234
DOI:10.1039/c7dt01370a