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Palladium‐Catalyzed Selective o ‐Bromination of Mesoionic 1,3‐Diphenyltetrazolium‐5‐olate: Switching the Directing Group from Nitrogen to Oxygen
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Abstract
Pd‐catalyzed bromination of mesoionic 1,3‐diphenyltetrazolium‐5‐olate (
1
) was developed. In the presence of palladium acetate (5 mol%),
N
‐bromosuccinimide (110 mol%), and
p
‐toluenesulfonic acid (50 mol%) in 1,2‐dichloroethane under reflux, olate
1
underwent bromination to give 1‐(2‐bromophenyl)‐3‐phenyltetrazolium‐5‐olate in a moderate yield as the major product, indicating that the 4‐nitrogen atom acts as a directing group rather than the negatively charged oxygen atom. The X‐ray‐suitable crystals of the corresponding palladacycle were isolated from 1‐mesityl‐3‐phentytetrazolium‐5‐olate and fully characterized. When both the
o
‐positions of the 3‐phenyl group were occupied by bromine atoms,
o
‐bromination then occurred at the 1‐phenyl group with the aid of the olate oxygen.
Title: Palladium‐Catalyzed Selective
o
‐Bromination of Mesoionic 1,3‐Diphenyltetrazolium‐5‐olate: Switching the Directing Group from Nitrogen to Oxygen
Description:
Abstract
Pd‐catalyzed bromination of mesoionic 1,3‐diphenyltetrazolium‐5‐olate (
1
) was developed.
In the presence of palladium acetate (5 mol%),
N
‐bromosuccinimide (110 mol%), and
p
‐toluenesulfonic acid (50 mol%) in 1,2‐dichloroethane under reflux, olate
1
underwent bromination to give 1‐(2‐bromophenyl)‐3‐phenyltetrazolium‐5‐olate in a moderate yield as the major product, indicating that the 4‐nitrogen atom acts as a directing group rather than the negatively charged oxygen atom.
The X‐ray‐suitable crystals of the corresponding palladacycle were isolated from 1‐mesityl‐3‐phentytetrazolium‐5‐olate and fully characterized.
When both the
o
‐positions of the 3‐phenyl group were occupied by bromine atoms,
o
‐bromination then occurred at the 1‐phenyl group with the aid of the olate oxygen.
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