With DBU-activated N-bromophthalimide as potential N-sources to achieve P-N cross-coupling of P(O)-H compounds

We have demonstrated that N-haloimides can be utilized as an aminating reagent, in addition to the traditional brominating reagent. Herein, the P-N cross-coupling of P(O)-H compounds and N-bromophthalimide has been developed with the DBU activation strategy. The nitrogen source may arise from internal N-bromophthalimide itself (a self-immolating reagent) or external phthalimide derivatives (with NBS-DBU activation system). The reaction features broad phosphorous compounds scope, including H-phosphinates, H-phosphonates, and H-phosphine oxides, and short reaction time (less than 10 min). This method provides a simple, convenient, efficient, and green route toward phosphoramidates which are of biological importance under mild conditions. (C) 2016 Elsevier Ltd. All rights reserved.