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Chemo-, regio-, and stereoselective tetrafunctionalization of fluoroalkynes enables divergent synthesis of 5-7-membered azacycles
被引:19
作者:

Chen, Jia-Wei
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机构:
Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Ji, Wen-Jun
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Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Huang, Xue-Ying
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机构:
Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Ge, Danhua
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机构:
Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Shen, Zhi-Liang
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Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Guo, Kai
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机构:
Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

Chu, Xue-Qiang
论文数: 0 引用数: 0
h-index: 0
机构:
Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
机构:
[1] Nanjing Tech Univ, Tech Inst Fluorochem, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
[2] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China
基金:
中国国家自然科学基金;
关键词:
F BOND FUNCTIONALIZATIONS;
C-H;
ACTIVATION;
ALKYNES;
HYDRODEFLUORINATION;
DIAMINATION;
CHEMISTRY;
ANILINES;
D O I:
10.1039/d4sc03230f
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Alkyne annulation has been widely used in organic synthesis for the construction of azacycles with unique structural and physicochemical properties. However, the analogous transformation of fluoroalkynes remains a challenge and has seen limited progress. Herein we report a 1,2,3,4-tetrafunctionalization of polyfluoroalkynes for the divergent construction of 5-7-membered (E)-1,2-difluorovinyl azacycles. The use of the fluorine atom as a detachable "activator" not only obviates the use of any transition metal catalysts and oxidizing reagents, but also ensures the [3-5 + 2]-annulation and defluorinative functionalization of fluoroalkynes with high chemo-, regio-, and stereoselectivities. This method exhibits a broad substrate scope, good functional group tolerance, and excellent scalability, providing a modular platform for accessing fluorinated skeletons of medicinal and biological interest. The late-stage modification of complex molecules, the multi-component 1,2-diamination of fluoroalkyne, and the synthesis of valuable organofluorides from the obtained products further highlight the real-world utility of this fluoroalkyne annulation technology. A 1,2,3,4-tetrafunctionalization of polyfluoroalkynes for the divergent construction of 5-7-membered (E)-1,2-difluorovinyl azacycles is developed.
引用
收藏
页码:12026 / 12035
页数:10
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[7]
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.
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Gree, Danielle
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Roisnel, Thierry
;
Caytan, Elsa
;
Hachem, Ali
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[9]
Copper-catalyzed 1,2-double amination of 1-halo-1-alkynes. Concise synthesis of protected tetrahydropyrazines and related heterocyclic compounds
[J].
Fukudome, Yasuhiro
;
Naito, Hiroyuki
;
Hata, Takeshi
;
Urabe, Hirokazu
.
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[10]
gem-Difluoromethylene Alkyne-Enabled Diverse C-H Functionalization and Application to the on-DNA Synthesis of Difluorinated Isocoumarins
[J].
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;
Lin, Shuang
;
Zhang, Shuning
;
Chen, Weijie
;
Liu, Xiawen
;
Yang, Guang
;
Lerner, Richard A.
;
Xu, Hongtao
;
Zhou, Zhi
;
Yi, Wei
.
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Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China Guangzhou Med Univ, Guangzhou Municipal & Guangdong Prov Key Lab Prot, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China

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