Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 1, Pages 176-179Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000581
Keywords
Rhodium(III)-catalysis; Quinoline-8-carboxaldehyde; Sulfoxonium ylides; Acylmethylation; Quinoline-1; 3-diketones
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Funding
- National Key Research and Development Program of China [2016YFD0300708]
- National Natural Science Foundation of China [21732002, 21672117, 21772104]
- Open Project Program of Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University (BTBU), Beijing, China [SPFW2019YB07]
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This study presents a new protocol for the rhodium(III)-catalyzed aldehydic C(sp(2))-H acylmethylation reactions, using sulfoxonium ylides as carbene precursors to generate 1,3-diketones from quinoline-8-carboxaldehydes. The reaction mechanism was elucidated by synthesizing a key intermediate - a five-membered-ring acylrhodium species.
Herein, we report a protocol for rhodium(III)-catalyzed aldehydic C(sp(2))-H acylmethylation reactions of quinoline-8-carboxaldehydes using sulfoxonium ylides as carbene precursors to afford 1,3-diketones, which readily tautomerized to their enol forms. We determined the reaction mechanism by synthesizing the key intermediate, a five-membered-ring acylrhodium species.
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