Ni-Catalyzed Kumada–Corriu Cross-Coupling Reactions of Tertiary Grignard Reagents and Bromostyrenes DOI
Kaidi Li,

Bing Zu,

Clément Mazet

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6047 - 6052

Published: July 9, 2024

The development of protocols for the construction congested quaternary centers is highly sought-after. Herein, we report a method cross-coupling C(sp

Language: Английский

Chromium‐Catalyzed Reductive Cross‐Coupling to Construct C−SS Bonds from Unactivated Alkyl Electrophiles DOI

Chao‐Peng Zhang,

Tian‐Zhang Wang,

Kang Wu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: March 15, 2024

Abstract Low‐valent chromium catalysts are cheap and less toxic compared to other transition metal catalysts. Here in, we reported a ligand‐free chromium(III)‐catalyzed manganese reductive cross‐coupling of unactivated alkyl electrophiles, such as sulfonates chlorides, with trisulfide dioxides thiolation agents form carbon−sulfur bonds. The powerful method featured ample substrate scope wide functional group tolerance, constructing large number unsymmetrical disulfides under simple conditions.

Language: Английский

Citations

7
Iron-Catalyzed Regioselective Reductive Fluoroalkylalkenylation of Unactivated Alkenes DOI
Siyu Wang,

Bohao Guo,

Tong Mu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(3), P. 1575 - 1583

Published: Jan. 16, 2024

The example of iron-catalyzed reductive fluoroalkylalkenylation unactivated alkenes has been disclosed, affording the stereodefined homoallylic fluoroalkanes with high efficiency and regioselectivity. This three-component cross-electrophile coupling features directing groups free, good functional group tolerance, broad substrate scope, late-stage difunctionalization biorelevant molecules. Moreover, this protocol sheds light on distinct reactivity disparities between fluoroalkyl nonfluoroalkyl radicals in cross-coupling reactions, highlighting unique nature iron/B2pin2 systems.

Language: Английский

Citations

5
Diastereo- and Enantioselective Dearomative Reductive Aryl-Fluoroalkenylation of Indoles by Nickel Catalysis DOI

Xinmiao Huang,

Min Ou,

Lixin Hong

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6432 - 6439

Published: April 11, 2024

Herein, we disclose a nickel-catalyzed dearomative reductive aryl-fluoroalkenylation of indoles by defluorinative coupling with gem-difluoroalkenes. The catalytic protocol affords facile assembly various monofluoroalkene-containing polycyclic fused indolines bearing two contiguous carbon stereocenters in high diastereo- and enantioselectivities tolerance diverse functional groups.

Language: Английский

Citations

5
The Progress of Reductive Coupling Reaction by Iron Catalysis DOI
Jian‐Qiang Zhao, Zhangpei Chen

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 17, 2024

Abstract The transition metal catalyzed coupling reaction has revolutionized the strategies for forging carbon‐carbon bonds. In contrast to traditional cross‐coupling methods using pre‐prepared nucleophilic organometallic reagents, reductive reactions C−C bonds formation provide some advantages. Because both partners are reduced in final products a stoichiometric amount of reductant, this approach not only avoids need use sensitive species, but also provides an orthogonal and complementary access classical reaction. Notably, feature readily available fragments, promote good step economy, exhibit high functional group tolerance unique chemoselectivity, which have propelled their increasingly popular organic synthesis. recent years, due low price, minimal toxicity, environmentally benign character, iron‐catalyzed garnered significant attention from synthetic chemists pharmacologists, especially coupling. This review aims insightful overview advances reactions, illustrate possible mechanisms.

Language: Английский

Citations

5
Ni-catalyzed cross-electrophile alkyl-alkyl coupling reactions DOI Creative Commons

Li-Xu You,

Tian Lan,

Chunling Guo

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 3, 2025

Language: Английский

Citations

0
Aryl halide cross-coupling via formate-mediated transfer hydrogenation DOI
Yoon Cho, Yu-Hsiang Chang, Kevin P. Quirion

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

Language: Английский

Citations

0
Iron-Catalyzed Reductive Cross-Coupling of Heterocyclic Bromides DOI

H JU,

Siyu Wang,

Bohao Guo

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7700 - 7709

Published: April 24, 2025

Language: Английский

Citations

0
Zinc Promoted Cross‐Electrophile Sulfonylation to Access Alkyl–Alkyl Sulfones DOI Creative Commons

Zhuochen Wang,

Rui Ma,

Chang Zhi Gu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(32)

Published: July 4, 2024

Abstract The transition metal‐catalyzed multi‐component cross‐electrophile sulfonylation, which incorporates SO 2 as a linker within organic frameworks, has proven to be powerful, efficient, and cost‐effective means of synthesizing challenging alkyl–alkyl sulfones. Transition metal catalysts play crucial role in this method by transferring electrons from reductants electrophilic organohalides, thereby causing undesirable side reactions such homocoupling, protodehalogenation, β ‐hydride elimination, etc. It is worth noting that tertiary alkyl halides have rarely been demonstrated compatible with current methods owing various undesired reactions. In work, zinc‐promoted sulfonylation developed through radical‐polar crossover pathway. This approach enables the synthesis sulfones, including 1°‐1°, 2°‐1°, 3°‐1°, 2°‐2°, 3°‐2° types, inexpensive readily available halides. Various functional groups are well tolerated resulting yields up 93%. Additionally, protocol successfully applied intramolecular homo‐sulfonylation insights gained work shall useful for further development access

Language: Английский

Citations

2
Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C–S Bond Cleavage DOI

Pingliang Zhu,

Yu Zhao,

Shaowen Ling

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12001 - 12009

Published: Aug. 15, 2024

Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C(sp2)–S bond cleavage under reductive conditions, thereby providing various biaryl frameworks high efficiency. Mechanistic studies suggested Mo(CO)6 played crucial role in facilitating the activation bond. This protocol demonstrated wide substrate scope, operational simplicity, and good functional group compatibility. Furthermore, utility this reaction was highlighted by facile scale-up sequential modification heteroaryl frameworks.

Language: Английский

Citations

2
Precision Propargylic Substitution Reaction: Pd-Catalyzed Suzuki–Miyaura Coupling of Nonactivated Propargylamines with Boronic Acids DOI
Yan Sun, Tao Zhao, Haixiang Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 31, 2024

Palladium-catalyzed Suzuki–Miyaura cross-coupling is an efficient approach for C–C bond construction. Here we report a deaminative reaction to achieve chemo- and regioselectivity in the of nonactivated propargylamines with boronic acids, which methyl propiolate introduced promote cleavage C–N form bond. This method features wide range substrates, good functional group tolerance, ease operation, providing alternative accessing valuable propargylated aromatic compounds.

Language: Английский

Citations

2