Carbometalation and Heterometalation of Carbon-Carbon Multiple-Bonds Using Group-13 Heavy Metals: Carbogallation, Carboindation, Heterogallation, and Heteroindation.

Organogallium and -indium compounds are useful reagents in organic synthesis because of their moderate stability, efficient reactivity and high chemoselectivity. Carbogallation and -indation of a carbon-carbon multiple bond achieves the simultaneous formation of carbon-carbon and carbon-metal bonds. Heterogallation and -indation construct carbon-heteroatom and carbon-metal bonds. Therefore, these reaction systems represent a significant synthetic method for organogalliums and -indiums. Many chemists have attempted to apply various types of unsaturated compounds such as alkynes, alkenes, and allenes to these reaction systems. This minireview provides an overview of carboindation and -gallation as well as heteroindation and -gallation.