期刊
CHEMICAL SCIENCE
卷 9, 期 16, 页码 4003-4008出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc00775f
关键词
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资金
- U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program [DE-SC0018222]
- U.S. Department of Energy (DOE) [DE-SC0018222] Funding Source: U.S. Department of Energy (DOE)
Substituted ureas have numerous applications but their synthesis typically requires the use of highly toxic starting materials. Herein we describe the first base-metal catalyst for the selective synthesis of symmetric ureas via the dehydrogenative coupling of methanol with primary amines. Using a pincer supported iron catalyst, a range of ureas was generated with isolated yields of up to 80% (corresponding to a catalytic turnover of up to 160) and with H-2 as the sole byproduct. Mechanistic studies indicate a stepwise pathway beginning with methanol dehydrogenation to give formaldehyde, which is trapped by amine to afford a formamide. The formamide is then dehydrogenated to produce a transient isocyanate, which reacts with another equivalent of amine to form a urea. These mechanistic insights enabled the development of an iron-catalyzed method for the synthesis of unsymmetric ureas from amides and amines.
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