期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 11, 页码 3368-3372出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811297
关键词
hydroaminomethylation; hydroformylation; multicatalytic; reductive amination; transfer hydrogenation
资金
- Office of Science, U.S. Department of Energy [DE-AC02-05CH1123]
- National Institutes of Health [5F32GM112312]
We report an approach to conducting the hydroaminomethylation of diverse alpha-olefins with a wide range of alkyl, aryl, and heteroarylamines at relatively low temperatures (70-80 degrees 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 H-2, 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.
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