共 97 条
Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis
被引:56
作者:

Cheng, Yuan-Yuan
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Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Yu, Ji-Xin
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Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Lei, Tao
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Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Hou, Hong-Yu
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Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Chen, Bin
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h-index: 0
机构:
Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Tung, Chen-Ho
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h-index: 0
机构:
Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

Wu, Li-Zhu
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h-index: 0
机构:
Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
机构:
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China
基金:
中国国家自然科学基金;
关键词:
alkenes;
diacylation;
photocatalysis;
reaction mechanisms;
synthetic methods;
C-H BORYLATION;
1,4-DICARBONYL COMPOUNDS;
CATALYZED FLUORINATION;
PHOTOREDOX CATALYSIS;
CONJUGATE ADDITION;
STETTER REACTION;
ACYLATION;
METAL;
ACIDS;
HYDROACYLATION;
D O I:
10.1002/anie.202112370
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)(4)(+) not only associates with the alkyl anion to avoid protonation, but also activates the alpha-keto acid to undergo electrophilic addition. The alpha-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.
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收藏
页码:26822 / 26828
页数:7
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