Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes

被引：0

作者：

Wang, Zhi-Shang ^{[1
]}

Hong, Dong-Guo ^{[1
]}

Li, Hongfang ^{[1
]}

Loh, Teck-Peng ^{[1
,3
]}

Lu, Ming-Zhu ^{[1
,2
]}

机构：

[1] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol, Zhengzhou 450001, Peoples R China

[2] Huaiyin Normal Univ, Sch Chem & Chem Engn, Huain 223300, Peoples R China

[3] Nanyang Technol Univ, Sch Chem Chem Engn & Biotechnol, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 17期

基金：

中国国家自然科学基金;

关键词：

C-H ARYLATION; DIFLUORINATED CYCLOPROPANES; FLUORINE; ACTIVATION; INDOLES; ACCESS; ALKENYLATION; ARENES; ARYL;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F bond cleavage. This regioselective ring-opening defluorinative Hiyama cross-coupling features a broad substrate scope with excellent functional group compatibility, affording a diverse variety of linear 2-fluoroallylic scaffolds in good yields with high Z-selectivity.

引用

页码：6054 / 6062

页数：9

共 90 条

[1] Palladium-Catalyzed Cross-Coupling of gem-Difluorocyclopropanes with gem-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes [J].

Ahmed, Ebrahim-Alkhalil M. A. ;

Zhang, Hongchen ;

Cao, Wen-Gen ;

Gong, Tian-Jun .

ORGANIC LETTERS, 2023, 25 (50) :9020-9024

[2] Access to Divergent Fluorinated Enynes and Arenes via Palladium-Catalyzed Ring-Opening Alkynylation of gem-Difluorinated Cyclopropanes [J].

Ahmed, Ebrahim-Alkhalil M. A. ;

Suliman, Ayman M. Y. ;

Gong, Tian-Jun ;

Fu, Yao .

ORGANIC LETTERS, 2020, 22 (04) :1414-1419

[3] Palladium-Catalyzed Stereoselective Defluorination Arylation/Alkenylation/Alkylation of gem-Difluorinated Cyclopropanes [J].

Ahmed, Ebrahim-Alkhalil M. A. ;

Suliman, Ayman M. Y. ;

Gong, Tian-Jun ;

Fu, Yao .

ORGANIC LETTERS, 2019, 21 (14) :5645-5649

[4] Cobalt-Catalyzed Fluoroallyllation of Carbonyls via C-C Activation of gem-Difluorocyclopropanes [J].

Ai, Yinan ;

Yang, Hanlin ;

Duan, Chunying ;

Li, Xingwei ;

Yu, Songjie .

ORGANIC LETTERS, 2022, 24 (28) :5051-5055

[5] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[6] Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol [J].

Bi, Lei ;

Georg, Gunda I. .

ORGANIC LETTERS, 2011, 13 (20) :5413-5415

[7] Cobalt-Catalyzed Hiyama-Type C-H Activation with Arylsiloxanes: Versatile Access to Highly ortho-Decorated Biaryls [J].

Bu, Qingqing ;

Gonka, Elzbieta ;

Kucinski, Krzysztof ;

Ackermann, Lutz .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (09) :2213-2216

[8] Palladium-catalyzed arylation of allylic benzoates using hypervalent siloxane derivatives [J].

Correia, R ;

DeShong, P .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7159-7165

[9] Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods [J].

Denmark, Scott E. ;

Regen, Christopher S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1486-1499

[10] Palladium-catalyzed cross-coupling reactions of silanolates: A paradigm shift in silicon-based cross-coupling reactions [J].

Denmark, Scott. E. ;

Baird, John D. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (19) :4954-4963

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