An electrochemical three component cascade phosphorylation reaction of various heteroatoms-containing nucleophiles including carbazoles, indoles, phenols, alcohols, and thiols with Ph 2 PH has been established. Electricity is used as the "traceless" oxidant and water and air are utilized as the "green" oxygen source. All kinds of structurally diverse organophosphorus compounds with P(O)-N/P(O)-O/P(O)-S bonds are assembled in moderate to excellent yields (three categories of phosphorylation products, 50 examples, up to 97 % yield). A tentative free radical course is put forward to rationalize the reaction procedure.

We report a direct and green electrochemical oxidative cross-dehydrogenative coupling reaction of N-heterocycles with hydrogen phosphoryl compounds under external oxidant-free conditions. Various phosphorylation products of substituted carbazoles and indoles are assembled in modest to excellent yields. A hydrogen release process is preliminarily demonstrated and H 2 is the sole byproduct. An imidazolium based ionic liquid is selected as the optimal electrolyte.

Functional groups are atoms or groups that determine the chemical properties of organic compounds. It often plays the role of guiding group in organic synthesis chemistry. Defunctionalization is the chemical transformation of a substrate with more functional groups into a compound with fewer functional groups, which has positive applications in solving environmental problems, resource shortage and biomass degradation. But due to the bond energy, heating, acid or base are often involved in defunctionalization. In recent years, defunctionalization has been moving toward a greener and more sustainable direction. Metal catalysis provides a new way for defunctionalization. The recent applications of different metalmediated defunctionalization in organic synthesis and their mechanism are summarized.