Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO

Cheng Ran; Zhao Hai-Yang; Zhang Shu; Zhang Xingang

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Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO

机译：镍催化的二氟甲基化，二氟甲基化，非氟化脂族电子药物与CO的1次ATM下的芳基硼酸的羰基化物

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摘要

The nickel-catalyzed carbonylation of aliphatic electrophiles with the most straightforward CO remains challenging. Here, we describe an example of the nickel-catalyzed carbonylation of secondary alkyl halides with arylboronic acids under 1 atm of CO. The reaction exhibits high functional group tolerance and a broad substrate scope, including trifluoromethylated, difluoromethylated, and difluoroacetylated secondary alkyl iodides and secondary benzyl bromides, providing a general and cost-efficient method to access alkyl ketones, especially alpha-trifluoromethylated alkyl ketones that are of great interest in medicinal chemistry. Preliminary mechanistic studies reveal that a bimetallic oxidative addition is likely involved in the reaction.

机译：脂族电子药物的镍催化的羰基化与最直接的CO保持挑战性。在此，我们描述了在1atm的1atm下与芳基硼酸的仲烷基卤化物的镍催化的羰基化的实例。该反应表现出高官能团耐受性和宽基底范围，包括三氟甲基化，二氟甲基化和二氟乙酰化的二次烷基碘和二级苄基溴化物，提供一般且经济效率的方法来获得烷基酮，特别是对药物化学感兴趣的α-三氟甲基化烷基酮。初步机械研究表明，反应可能参与双金属氧化添加。

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来源
《ACS catalysis》 |2020年第1期|共7页
作者
Cheng Ran; Zhao Hai-Yang; Zhang Shu; Zhang Xingang;
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作者单位

Univ Chinese Acad Sci Shanghai Inst Organ Chem Ctr Excellence Mol Synth Key Lab Organofluorine Chem Chinese Acad Sci 345 Lingling Lu Shanghai 200032 Peoples R China;

Univ Chinese Acad Sci Shanghai Inst Organ Chem Ctr Excellence Mol Synth Key Lab Organofluorine Chem Chinese Acad Sci 345 Lingling Lu Shanghai 200032 Peoples R China;

Univ Elect Sci &

Technol China Sch Mat &

Energy 2006 Xiyuan Ave Chengdu 611731 Sichuan Peoples R China;

Univ Chinese Acad Sci Shanghai Inst Organ Chem Ctr Excellence Mol Synth Key Lab Organofluorine Chem Chinese Acad Sci 345 Lingling Lu Shanghai 200032 Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
alkyl ketones; carbonylation; CO; nickel; secondary aliphatic electrophiles;

机译：烷基酮;羰基化;CO;镍;二级脂族电泳;

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专利

1. Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO [J] . Cheng Ran, Zhao Hai-Yang, Zhang Shu, ACS catalysis . 2020,第1期

机译：镍催化的二氟甲基化，二氟甲基化，非氟化脂族电子药物与CO的1次ATM下的芳基硼酸的羰基化物
2. Nickel-catalyzed carbonylation of arylboronic acids with DMF as a CO source [J] . Yang Li, Dong-Huai Tu, Bo Wang Organic Chemistry Frontiers . 2017,第4期

机译：用DMF作为CO源镍催化的芳基硼酸的羰基化
3. Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source [J] . Hamaguchi Takashi, Takahashi Yoshiyuki, Tsuji Hiroaki, Organic letters . 2020,第3期

机译：镍催化的原位的芳基硼酸的1,3-二烯用仲优质碳酸酯作为1,3-二烯和氢化物源的替代物
4. APPLICATIONS OF FOLIC ACID IN SECONDARY WASTEWATER TREATMENT [C] . Etienne Dubé, Daniel Gagnon, Henri-Claude Lavallée, TAPPI international environmental conference and exhibit . 2002

机译：叶酸在二次废水处理中的应用
5. Nickel-Catalyzed Negishi Cross-Couplings of Secondary Nucleophiles with Secondary Propargylic Electrophiles at Room Temperature [O] . Sean W. Smith, Gregory C. Fu -1

机译：室温下镍催化次级亲核试剂与次级炔丙基亲电试剂的Negishi交叉偶联
6. Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids [O] . Gregory C. Fu 2006

机译：氨基醇作为镍催化的未活化烷基卤化物（包括仲烷基氯化物）与芳基硼酸的suzuki反应的配体

Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO

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