Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 18, Pages 4354-4359Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100633
Keywords
5-acyl-3-furancarboxaldehydes; [3+2] annulation; N,N-dimethyl enaminones; regio- and chemoselective
Categories
Funding
- National Natural Science Foundation of China [21961018]
- Natural Science Foundation of Yunnan Province [201901T070302]
- Analytical AMP
- Testing Foundation of Kunming University of Science and Technology [2020M20192218003]
- Plan of Funding Out-standing Young Talents of Yunnan Province
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A copper(II)-mediated intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed, providing access to 5-acyl-3-furancarboxaldehydes with good yields and broad substrate scope. This reaction allows the formation of multiple new bonds through a radical cyclization process, showing potential application value in industry as demonstrated by gram-scale synthesis and application research.
Copper(II)-mediated unprecedented intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed. The protocol is promoted simply by copper(II) chloride to access 5-acyl-3-furancarboxaldehydes with acceptable to good yields and broad substrate scope. This reaction allows the formation of multiple new bonds, including C(sp(2))-O bond between two nucleophilic sites, C(sp(2))-C(sp(2)) bond and C=O bond, through a radical cyclization process. Moreover, gram-synthesis and application research show the potential application value of this transformation in industry.
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