Chinese Journal of Organic Chemistry >
Palladium-Catalyzed Allylic Carbonylative Negishi Cross-Coupling Reactions with Sterically Bulky Aromatic Isocyanides
Received date: 2021-01-15
Revised date: 2021-02-01
Online published: 2021-02-26
Supported by
National Natural Science Foundation of China(21702060); Fundamental Research Funds for the Central Universities.; Shanghai Rising-Star Program, the Shanghai Municipal Science and Technology Major Project(2018SHZDZX03); Program of Introducing Talents of Discipline to Universities(B16017)
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 β-H elimination in carboxylation reaction, affords synthetically important β,γ-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.
Key words： palladium catalysis; carbonylation; isocyanide; β,γ-unsaturated ketones
Yangyang Weng , Jingping Qu , Yifeng Chen . Palladium-Catalyzed Allylic Carbonylative Negishi Cross-Coupling Reactions with Sterically Bulky Aromatic Isocyanides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 1949 -1956 . DOI: 10.6023/cjoc202101021
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