THREE-COMPONENT REACTIONS OF UNSATURATED COMPOUNDS WITH ARENEDIASONIUM SALTS AND NEUTRAL NUCLEOPHILS. ARYLSULFONYLATION

Abstract

The results of recent achievements on the interaction of arenediazonium salts with unsaturated compounds in the presence of neutral nucleophiles are summarized. New examples of multicomponent transformations with the participation of such neutral nucleophiles as CO (arylcarbonylation), NO (arylnitrosylation), aceto¬nitrile (aminoarylation), SO2 (arylsulfonylation) and others are given. These reactions can be applied to alkenes, alkynes, aromatic compounds. Mild reaction conditions allow the use of reagents with different functional groups. Reactions of this type open up the possibility of one-step production of complex poly¬functional compounds. Catalytic systems are quite diverse for these transformations: it is catalysis involving transition metals, platinum group metals. Prospects for the use of arenediazonium salts in multicomponent transfor¬ma-tions according to the concepts of «green» chemistry are outlined – it is photoinitiation by visible and ultraviolet radiation, acid-base catalysis. The role of catalysis in the process, the role of complex intermediates and reaction mechanisms are analyzed. For most processes, the SET reaction mechanism is implemented through the formation of an alkene intermediate ion radical, the stability of which depends on the nature of the substituent near the double bond. Particular attention is paid to arylsulfonylation reactions, because the arylsulfonyl group is one of the many important biologically active molecules. Arylsulfonylation reactions of alkenes with the participation of transition metals or under conditions of metal-free catalysis are considered. Examples of arylsulfonylation of the C=C bond using sulfinic acids, their salts and hydrazides are given. An available method for producing functionalized sulfones is the multicomponent interaction of arenediazonium salts, alkenes and SO2. The arylsulfonylation reaction occurs as a series of successive reactions involving the generation of a catalyst, the decomposition of arenediazonium cations, the addition of an aryl group, a nucleophile to a multiple bond, and the formation of the final products. The use of functionalized alkenes allows to obtain functionalized arylsulfones in one step. This functionalization expands the scope of use of arylsulfones, in particular, for studies of biological activity. The progress made in the development of effective strategies for the production of arylsulfones opens new opportunities for further research.