期刊
ACS CATALYSIS
卷 12, 期 15, 页码 9664-9669出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c02569
关键词
monocarbonylation; double-carbonylation; cobalt catalysis; copper catalysis; alkanes
资金
- National Key R&D Program of China [2021YFA1500104]
- National Natural Science Foundation of China [22031008]
- Science Foundation of Wuhan [2020010601012192]
- Institution Fund Projects Grant [IFPIP 438-135-1442]
- Ministry of Education and King Abdulaziz University, DSR, Jeddah, Saudi Arabia
This work demonstrated metal-controlled mono-and double-carbonylation reactions of alkanes with amines, resulting in the preparation of alkyl amides and alkyl alpha-ketoamides, with Co and Cu catalysis systems affording different selectivities.
The control of reaction selectivity is a core of organic synthesis, which requires the rational design of the catalytic system. Carbonylation reactions involving CO, such as mono-carbonylation and double-carbonylation, are some of the most powerful tools for constructing carbonyl compounds. However, tunable mono-and double-carbonylation still remain a great challenge, especially for C-H bonds. In this work, we introduced metal-controlled mono-and double-carbonylation reactions of alkanes with amines to prepare alkyl amides and alkyl alpha- ketoamides, respectively (58 examples, yields up to 99%). The Co catalysis system afforded solely monocarbonylation products, and the Cu catalysis system afforded highly selective double-carbonylation products (more than 20:1). Only the choice of the Co or Cu catalyst precursor was the key to producing a dramatic switch in the reaction selectivity.
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