Halogen-metal exchange in 1,2-dibromobenzene and the possible intermediacy of 1,2-dilithiobenzene.
The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine-lithium exchange and subsequent derivatization reactions to operate.
Bettinger
Holger F
HF
Lehrstuhl für Organische Chemie 2, Ruhr-Universität Bochum, Universitätsstrasse 150, 44780 Bochum, Germany. holger.bettinger@rub.de
Filthaus
Matthias
M
D001555:Benzene Derivatives / Q000737:chemistry*; D001969:Bromobenzenes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
C526562:1,2-bis(trimethylsilyl)benzene; C526561:1,2-dilithiobenzene; D001555:Benzene Derivatives; D001969:Bromobenzenes; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C102879:1,2-dibromobenzene; D008094:Lithium