期刊
CHINESE JOURNAL OF ORGANIC CHEMISTRY
卷 41, 期 5, 页码 1949-1956出版社
SCIENCE PRESS
DOI: 10.6023/cjoc202101021
关键词
palladium catalysis; carbonylation; isocyanide; beta,gamma-unsaturated ketones
资金
- National Natural Science Foundation of China [21702060]
- Shanghai Rising-Star Program
- Shanghai Municipal Science and Technology Major Project [2018SHZDZX03]
- Program of Introducing Talents of Discipline to Universities [B16017]
- Fundamental Research Funds for the Central Universities
This study demonstrates the palladium-catalyzed allylic carbonylative Negishi cross-coupling reaction using sterically bulky aromatic isocyanides as a CO surrogate, leading to β,γ-unsaturated ketones with high regioselectivity and stereoselectivity. The advantages of this method include mild reaction conditions and a wide substrate scope due to the utilization of Negishi reagents as carbon nucleophiles.
Herein, the palladium-catalyzed allylic carbonylative Negishi cross-coupling reaction employing sterically bulky aromatic isocyanides as the CO surrogate was disclosed. The leverage of sterically bulky aromatic isocyanide minimizes the side beta-H elimination in carboxylation reaction, affords synthetically important beta,gamma-unsaturated ketones with high regioselectivity and stereoselectivity, thereby tackles the long-standing challenge in Pd-catalyzed allylic carbonylative cross-coupling with CO gas. Moreover, this protocol exhibits the advantage including mild reaction conditions, as well as broad substrate scope due to the utilization of Negishi reagent as the carbon nucleophiles.
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