In the transition metal-catalyzed cross-coupling reactions,phenol and enol derivatives activated by phosphorus groups are very important electrophiles.This kind of compounds has the advantages of easy preparation,great stability,and producing more benign phosphorus by-products.The present work provides a comprehensive review of the advances made over the past several decades in this area.Cross-coupling reactions mediated by PyBroP are first surveyed,then two types of recently developed transition metal-catalyzed reactions,i.e.,Pd-catalyzed and Nicatalyzed reactions,and the corresponding mechanisms are discussed.Finally,future directions are analyzed. In the transition metal-catalyzed cross-coupling reactions, phenol and enol derivatives activated by phosphorus groups are very important electrophiles. This kind of compounds has has advantages of easy preparation, great stability, and producing more benign phosphorus by-products. The present work provides a comprehensive review of the advances made over the past several decades in this area. Cross-coupling reactions mediated by PyBroP are first surveyed, then two types of recently developed transition metal-catalyzed reactions, ie, Pd-catalyzed and Nicatalyzed reactions, and the corresponding mechanisms are discussed .Finally, future directions are analyzed.