The mechanisms of the Stille reaction.
Eighteen years ago in Angewandte Chemie John K. Stille reviewed a novel methodology, which eventually became known by his name, for the coupling of organostannanes with organic electrophiles. Since then that seed has blossomed into a multifaceted methodology full of hidden possibilities to explore, discover, and enjoy. Very recent modifications are making synthetic wishes come true that were only dreamed of a few years ago. Moreover, as important advances are being made in the understanding of the mechanistic details of the process, it is becoming increasingly possible to apply this essential reaction and its new variants in a less empirical way. The purpose of this Review is to give a critical account of this progress.
Espinet
Pablo
P
Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47005, Spain. espinet@qi.uva.es
Echavarren
Antonio M
AM
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009947:Organotin Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D006846:Hydrocarbons, Halogenated; D008024:Ligands; D009942:Organometallic Compounds; D009947:Organotin Compounds; D010165:Palladium; D002244:Carbon; D003300:Copper