Carboberyllation: addition of organoberyllium species to alkenes and alkynes. A comparison with carboboration. Issue 24 (23rd May 2017)

• Record Type: Journal Article
• Authors: Field-Theodore, Terri E.; Couchman, Shannon A.; Wilson, David J. D.; Dutton, Jason L.
• Is Part Of: Dalton transactions. Volume 46:Issue 24(2017)
• Page Start: 7686
• Page End: 7692
• Publication Date: 2017-05-23
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c7dt01370a
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : 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. 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.