A Multicatalytic Approach to the Hydroaminomethylation of ?-Olefins.

ABSTRACT: We report an approach to conducting the hydroaminomethylation of diverse ?-olefins with a wide range of alkyl, aryl, and heteroarylamines at relatively low temperatures (70-80?°C) and pressures (1.0-3.4?bar) of synthesis gas. This approach is based on simultaneously using two distinct catalysts that are mutually compatible. The hydroformylation step is catalyzed by a rhodium diphosphine complex, and the reductive amination step, which is conducted as a transfer hydrogenation with aqueous, buffered sodium formate as the reducing agent, is catalyzed by a cyclometallated iridium complex. By adjusting the ratio of CO to H2 , we conducted the reaction at one atmosphere of gas with little change in yield. A diverse array of olefins and amines, including hetreroarylamines that do not react under more conventional conditions with a single catalyst, underwent hydroaminomethylation with this new system, and the pharmaceutical ibutilide was prepared in higher yield and under milder conditions than with a single catalyst.

SUBMITTER: Hanna S 

PROVIDER: S-EPMC6548469 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature