Abstract
Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.
Highlights
Showcasing research from the group of Dr Suguru Yoshida and Professor Takamitsu Hosoya at the Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), Japan and the group of Dr Isao Kii at RIKEN, Japan
In the course of our recent studies regarding phosphorus chemistry[8] and molecular conjugation chemistry,[9] we revisited the Staudinger reaction between aromatic azides and various phosphines.8b These studies gave us an idea of preparing an aza-ylide that would be stable toward hydrolysis and oxidation
After extensive screening of aromatic azides for the Staudinger reaction with triphenylphosphine in the presence of water, we found that 2,6-dichlorophenyl azide was efficiently transformed to the corresponding aza-ylide without the formation of the aniline derivative (Table 1)
Summary
Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines.
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