Palladium-Catalyzed Allylic Carbonylative Negishi Cross-Coupling Reactions with Sterically Bulky Aromatic Isocyanides

doi:10.6023/cjoc202101021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1949-1956.DOI: 10.6023/cjoc202101021 Previous Articles Next Articles

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钯催化大位阻芳基异腈作为羰基源的烯丙基羰基化Negishi偶联反应

翁扬扬¹, 曲景平¹, 陈宜峰¹^,^*()

1 华东理工大学化学与分子工程学院费林加诺贝尔奖科学家联合研究中心材料生物学与动态化学前沿科学中心上海 200237

收稿日期:2021-01-15 修回日期:2021-02-01 发布日期:2021-02-26
通讯作者: 陈宜峰
基金资助:
国家自然科学基金(21702060); 中央高校基本科研基金资助项目.; 上海市重大科技专项(2018SHZDZX03); 高等学校学科创新引智计划(B16017)

Palladium-Catalyzed Allylic Carbonylative Negishi Cross-Coupling Reactions with Sterically Bulky Aromatic Isocyanides

Yangyang Weng¹, Jingping Qu¹, Yifeng Chen¹^,^*()

1 Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237

Received:2021-01-15 Revised:2021-02-01 Published:2021-02-26
Contact: Yifeng Chen
About author:
* Corresponding author. E-mail: yifengchen@ecust.edu.cn
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)

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Abstract

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

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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.

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Fig. & Tab. 5

Scheme 1. Pd-catalyzed allylic carbonylative reaction

Entry LG Isocyanide2 [Pd] catalyst Yield^b/%

Table 1. Optimization of Conditionsa

Table 2. Scope of alkyl zinc reagentsa

Table 3. Scope of allylic phosphatesa

Scheme 2. Proposed mechanism

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钯催化大位阻芳基异腈作为羰基源的烯丙基羰基化Negishi偶联反应

Palladium-Catalyzed Allylic Carbonylative Negishi Cross-Coupling Reactions with Sterically Bulky Aromatic Isocyanides

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Fig. & Tab. 5

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