期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 20, 页码 13112-13123出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02299
关键词
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资金
- European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie Actions Grant [837718]
- COST action [CA15106]
- Research Foundation-Flanders (FWO) [30902231]
- Hercules Foundation
- Marie Curie Actions (MSCA) [837718] Funding Source: Marie Curie Actions (MSCA)
An efficient strategy for the cleavage of the picolinamide directing group (DG) and recycling of the byproduct generated has been developed. In this protocol, picolinamides were first Boc activated into tertiary N-Boc-N-substituted picolinamides. These were then cleaved via a Ni-catalyzed esterification reaction with EtOH to give valuable N-Boc protected amines. Ni(cod)(2) was used as a catalyst without any ligands or base additives. The byproduct, ethyl 2-picolinate can be used to install the picolinamide DG in a direct or indirect manner on amines. The protocol exhibits a broad functional group tolerance and high yields. To demonstrate the utility of this approach, it was applied on many selected examples from the recent C-H functionalization literature featuring 2-picolinamide as a DG.
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