Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 50, Pages 20378-20383Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja207389z
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Funding
- U.S. Department of Energy, Basic Energy Sciences [DE-FG02-84-ER13289]
- National Science Foundation, Division of Chemistry, Analytical and Surface Science [CHE-0952790]
- Harvard University Center for the Environment through the Graduate Consortium in Energy and the Environment
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We have discovered that metallic gold is a highly effective vehicle for the low-temperature vapor-phase carbonylation of methanol by insertion of CO into the O-H bond to form methoxycarbonyl. This reaction contrasts sharply to the carbonylation pathway well known for homogeneously catalyzed carbonylation reactions, such as the synthesis of acetic acid. The methoxycarbonyl intermediate can be further employed in a variety of methoxycarbonylation reactions, without the use or production of toxic chemicals. More generally we observe facile, selective methoxycarbonylation of alkyl and aryl alcohols and secondary amines on metallic gold well below room temperature. A specific example is the synthesis of dimethyl carbonate, which has extensive use in organic synthesis. This work establishes a unique framework for using oxygen-activated metallic gold as a catalyst for energy-efficient, environmentally benign production of key synthetic chemical agents.
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