Iron-Catalyzed C–C Bond Cleavage of Oximes for Direct Coupling of Benzothiazole in Water DOI

Wuxin Zhou,

Yang Long, Haifeng Xiang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4875 - 4879

Published: March 29, 2023

An Fe-catalyzed coupling reaction between oxime ester and benzothiazole is described, which involves C-C bond cleavage of via a single-electron transfer process. This iron catalytic system performed in water under mild conditions offers streamlined strategy to the construction alkyl nitrile substituted derivatives. Application this for synthesis some key important compounds including 4-heterocyclic-3-arylbutanoic acid also reported.

Language: Английский

Double strain-release enables formal C–O/C–F and C–N/C–F ring-opening metathesis DOI Creative Commons

Yulei Zhu,

Jie Jia,

Xiangyu Song

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13800 - 13806

Published: Jan. 1, 2024

Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved double-bond metathesis, like olefin metathesis and carbonyl single-bond has received less attention the past decade. Herein, we describe first C(sp

Language: Английский

Citations

5
Lewis Acid-Catalyzed Ring-Opening Cross-Coupling Reaction of gem-Difluorinated Cyclopropanes Enabled by C–F Bond Activation DOI
Xiuli Wu, Yaxin Zeng, Zhong‐Tao Jiang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8429 - 8434

Published: Nov. 4, 2022

gem-Difluorinated cyclopropanes have attracted wide research interest in organic synthesis due to their high reactivity. Herein, we report a Lewis acid-catalyzed cross-coupling reaction of mono- and disubstituted gem-difluorinated with nucleophiles. The formation fluoroallyl cation species triggered via the acid-assisted activation C-F bond is proposed this transformation. then trapped by nucleophiles, including electron-rich arenes allylsilanes, deliver series fluoroallylic products good yields. provides an alternative mode for using as surrogates.

Language: Английский

Citations

22
Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution DOI
Zhong‐Tao Jiang,

Zhengzhao Chen,

Yaxin Zeng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(33), P. 6176 - 6181

Published: Aug. 11, 2022

Herein, we report an effective method to offer chiral gem-difluorinated cyclopropanes containing all-carbon quaternary stereocenter by rhodium-catalyzed stereoablative kinetic resolution. The activation of a sterically hindered C–C bond through oxidative addition with rhodium complex is proposed as the enantiodetermining step. A wide range can be obtained excellent ee values (ee = 87% >99.9%), which are demonstrated useful fluorine-containing building blocks series postfunctionalizations.

Language: Английский

Citations

20
Diversified Synthesis of All-Carbon Quaternary gem-Difluorinated Cyclopropanes via Copper-Catalyzed Cross-Coupling DOI
Bin Li,

Jiang‐Ling Shi,

Ying Xia

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2674 - 2679

Published: April 11, 2023

The construction of all-carbon quaternary centers in small-ring systems is important but challenging organic synthesis. Herein, by taking gem-difluorocyclopropyl bromides (DFCBs) as a type general and versatile building block, we developed practical method for gem-difluorinated cyclopropanes (DFCs). reaction relies on the involvement radical intermediate, which can couple with wide range nucleophiles under copper catalysis.

Language: Английский

Citations

12
Electrocarboxylation of CO2 with Organic Substrates: Toward Cathodic Reaction DOI

He Yao,

Mei‐Yan Wang, Chengguang Yue

et al.

Transactions of Tianjin University, Journal Year: 2023, Volume and Issue: 29(4), P. 254 - 274

Published: July 3, 2023

Language: Английский

Citations

11
Nickel-Catalyzed Reductive Arylation of gem-Bromofluorocyclopropanes To Construct Monofluorinated Cyclopropane Derivatives DOI
Wen Zhang, Yuheng Huang,

Tian-Rui Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

A nickel-catalyzed reductive cross-coupling of gem-bromofluorocyclopropanes with aryl bromides for the synthesis monofluorinated cyclopropane derivatives is reported. Different from cleavage route ring reported by previous works, this catalytic system shows excellent regioselectivity control cyclic selectivity, giving as major product. This transformation demonstrates mild conditions, high efficiency, a broad substrate scope, and good functional group compatibility, providing facile method diversified cyclopropane-containing drugs bioactive molecules.

Language: Английский

Citations

0
(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds DOI
Neeraj Yadav, Prabal Banerjee

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Herein, we present an acid- and base-mediated approach for ring opening of donor-acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant gem-difluorinated cyclopentenes via α,α-difluoroketone scaffolds. Fluorinated rings are essential building blocks in drug discovery materials research. This methodology has a broad substrate scope, is scalable, provides practical synthetic route to obtain value-added fluorinated compounds.

Language: Английский

Citations

0
Palladium-catalyzed cross-coupling of gem-difluorocyclopropanes with gem-diborylalkanes: facile synthesis of a diverse array of gem-diboryl-substituted fluorinated alkenes DOI Creative Commons
Ebrahim‐Alkhalil M. A. Ahmed,

Hongchen Zhang,

Wen-Gen Cao

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(13), P. 10265 - 10272

Published: Jan. 1, 2025

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of gem -difluorinated cyclopropanes with array -diborylalkanes under mild reaction conditions.

Language: Английский

Citations

0
Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes DOI

Zimin Wang,

Daniel C. Hong,

Hongfang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

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 cleavage. This regioselective features a broad substrate scope excellent functional group compatibility, affording variety linear 2-fluoroallylic scaffolds in good yields high Z-selectivity.

Language: Английский

Citations

0
Pd-IPent-Catalyzed Defluorinative Annulation of gem-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted N-H Pyrroles DOI
Wenhao Liu,

Yahui Ma,

Qiuwei Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of gem-difluorocyclopropanes with enamides, which provides convenient and efficient strategy for the synthesis multisubstituted N-H pyrrole derivatives. This transformation selectively cleaves C1-C3 bond, two C-F bonds, C-N bond in one-pot procedure. Additionally, this protocol allows modification several bioactive molecules.

Language: Английский

Citations

0