The Stille reaction is an extremely versatile
alternative to the Suzuki reaction. It
replaces the organoboron reagents with
organostannanes. As the tin bears four organic
functional groups, understanding the rates of
transmetallation of each group is important.
Relative rate of transmetallation:
Alkynyl>vinyl>aryl>allyl~benzyl>>alkyl
The Stille coupling is particularly popular as
organostannanes are readily prepared, purified
and stored. The reaction also has the advantage
that it is run under neutral conditions making
it even more tolerant of different functional
groups than the Suzuki reaction.