Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 21, Pages 5942-5948Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01143c
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Funding
- National Natural Science Foundation of China [21801206]
- Chunhui Program of Ministry of Education of China [5180210003]
- Program for Young Talents of Shaanxi Province [5113190023]
- Joint Research Funds of Department of Science & Technology of Shaanxi Province
- Northwestern Polytechnical University [2020GXLH-Z-015]
- Natural Science Basic Research Program of Shaanxi [2021JM-049]
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This paper reports a ruthenium-catalyzed cross-coupling reaction of long-range alkenyl alcohols with amines, achieving remote site-selective functionalization through a chain-walking strategy. The method exhibits good yields and functional group tolerance.
The long-range isomerization/transformation of alkenyl alcohols represents one of the most important classes of chemical transformations, but related remote amidations with amines are scarce. Herein, we report a redox-neutral Ru-catalyzed cross-coupling reaction of long-range alkenyl alcohols with amines to produce the corresponding amides by a chain-walking strategy which is a powerful approach to realize remote site-selective functionalization. The catalyzed movement of an alkene double bond in alkenyl alcohols over 9 positions along an alkyl chain has been realized. A range of easily accessible alkenyl alcohols can be converted in a rapidly assembled fashion to valuable amides with good yields and wide functional group tolerance.
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