期刊
CHEMICAL SCIENCE
卷 10, 期 43, 页码 10089-10096出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc03672e
关键词
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资金
- Program for China Scholarship Council [201806360122]
- National Natural Science Foundation of China [21372258]
- Beijing National Laboratory for Molecular Sciences [BNLMS201845]
- US National Science Foundation [CHE-1902509]
A versatile Rh(i)-catalyzed C6-selective decarbonylative C-H alkenylation of 2-pyridones with readily available, and inexpensive alkenyl carboxylic acids has been developed. This directed dehydrogenative cross-coupling reaction affords 6-alkenylated 2-pyridones that would otherwise be difficult to access using conventional C-H functionalization protocols. The reaction occurs with high efficiency and is tolerant of a broad range of functional groups. A wide scope of alkenyl carboxylic acids, including challenging conjugated polyene carboxylic acids, are amenable to this transformation and no addition of external oxidant is required. Mechanistic studies revealed that (1) Boc(2)O acts as the activator for the in situ transformation of the carboxylic acids into anhydrides before oxidative addition by the Rh catalyst, (2) a decarbonylation step is involved in the catalytic cycle, and (3) the C-H bond cleavage is likely the turnover-limiting step.
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