Open AccessTin-Free Radical Carboazidation
Author(s) -
Philippe Panchaud,
Philippe Renaud
Publication year - 2004
Publication title -
chimia
Language(s) - English
Resource type - Journals
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/000942904777677920
Subject(s) - triethylborane , alkene , reagent , tin , environmentally friendly , chemistry , azide , radical initiator , radical , organic chemistry , combinatorial chemistry , catalysis , ecology , polymer , polymerization , biology
The radical carboazidation of alkenes could be achieved in water using triethylborane as initiator. This efficient process is complete in one hour at room temperature in an open system. These new tin-free azidation and carboazidation conditions are environmentally friendly and enable reactions to be run with an excess of either the alkene or the radical precursor. Furthermore, 3-pyridinesulfonyl azide could be used in order to avoid tedious purifications, especially when the reaction product has a similar chromatographic behavior to benzenesulfonyl azide, our original azidation reagent.