ille ▁reaction ▁is ▁a ▁chemical ▁reaction ▁widely ▁used ▁in ▁organ ic ▁synth esis . ▁The ▁involves ▁the ▁coupling ▁of ▁two ▁organ ic ▁groups , ▁one ▁of ▁which ▁is ▁carried ▁as ▁an ▁organ ot in ▁comp ound ▁( also ▁known ▁as ▁organ ost ann anes ). ▁ ▁A ▁variety ▁organ ic ▁elect roph iles ▁provide ▁the ▁other ▁coupling ▁partner . ▁The ▁St ille ▁reaction ▁is ▁one ▁of ▁many ▁p all ad ium - catal yz ed ▁coupling ▁re actions . ▁▁ ▁: ▁sp ^ 2 ▁hy brid ized ▁C ▁( ally l , ▁al ken yl , ▁or ▁ar yl ). ▁: ▁hal ides ▁( Cl , ▁Br , ▁I ), ▁pseud oh al ides ▁( , ▁OP O ( OR ) 2 ) ▁The ▁R 1 ▁group ▁attached ▁to ▁the ▁tri alk y lt in ▁is ▁normally ▁sp 2 - hy brid ized , ▁including ▁vin yl , ▁and ▁ar yl ▁groups . ▁▁▁ ▁These ▁organ ost ann anes ▁are ▁also ▁stable ▁to ▁both ▁air ▁and ▁mo ist ure , ▁and ▁many ▁of ▁these ▁re ag ents ▁either ▁are ▁commer cially ▁available ▁or ▁can ▁be ▁synth es ized ▁from ▁literature ▁preced ent . ▁ ▁However , ▁these ▁tin ▁re ag ents ▁tend ▁to ▁be ▁highly ▁to xic . ▁ ▁X ▁is ▁typically ▁a ▁hal ide , ▁such ▁as ▁Cl , ▁Br , ▁or ▁I , ▁yet ▁pseud oh al ides ▁such ▁as ▁trif l ates ▁and ▁sul fon ates ▁and ▁ph osph ates ▁can ▁also ▁be ▁used . ▁Several ▁reviews ▁have ▁been ▁published