Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates DOI

Liang Zou,

Huimin Yang, Tian Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15822 - 15833

Published: Oct. 18, 2024

Herein, we report a general and efficient Ni-catalyzed reductive cross-coupling reaction of substituted vinyl bromides α-chloro phosphonates to access set α-vinyl using zinc as the terminal reductant. This exhibits broad substrate adaptability good functional group tolerance, which allows afford diverse compounds including structurally complex motifs from natural products drugs. Furthermore, practicality was certificated through gram-scale transformation experiments. The preliminary mechanistic investigations support radical chain process. potential realize enantiomeric control makes it more valuable for further exploration.

Language: Английский

Dual Nickel- and Photoredox-Catalyzed Asymmetric Reductive Cross-Couplings: Just a Change of the Reduction System? DOI

Wenhao Xu,

Tao Xu

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: 57(14), P. 1997 - 2011

Published: July 4, 2024

ConspectusIn recent years, nickel-catalyzed asymmetric coupling reactions have emerged as efficient methods for constructing chiral C(sp

Language: Английский

Citations

8
Ni-catalyzed reductive alkylgermylation of activated alkenes: Modular access to polyfunctionalized alkyl germanes DOI Creative Commons

Yi-Wei Qiao,

Bing-Qi Zhou,

Yuan Huang

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(12), P. 100819 - 100819

Published: Nov. 22, 2023

Language: Английский

Citations

11
Direct Synthesis of β-Amino Boronates via Amide α-C–H Bond Activation and C(sp3)–C(sp3) Coupling under Dual Ni/Photoredox Catalysis DOI

Zihao Hu,

Dong Wang, Tao Xu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 547 - 553

Published: Dec. 26, 2023

Direct transformations of readily available amines or amides via C–H bond functionalization could provide a fast route for accessing complex molecules. While various groups have been successfully incorporated into the α position nitrogen atom with photoredox system activation, couplings functionalized alkyl halides are still very challenging. Herein, we report direct and convenient protocol β-amino boronates through C(sp3)–C(sp3) coupling α-bromoboronates. The mild conditions allow good functional group tolerance broad scope. application method in late-stage modification molecules further demonstrates its great potential organic synthesis. Mechanistic studies were also conducted, catalytic cycle is proposed.

Language: Английский

Citations

11
Synthesis of Chiral 3-Piperidin-2-ones and 3-Piperidines via Ni-Catalyzed Reductive Coupling DOI
Zhaoqing Wang, Z. Y. Zhang, Rui Liu

et al.

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

Published: May 13, 2025

Herein, an approach to a wide range of chiral 3-substituted δ-lactams from reductive coupling Csp2-hybridized organohalides and 3-chloro-δ-lactams was described, the products are versatile precursors for accessing enantioenriched piperidines. The utility reaction highlighted by economic synthesis Preclamol Niraparib. Notably, modified Bilm ligands were found be key factor reactivity enantioselectivity.

Language: Английский

Citations

0
Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp3) and C(sp)-C(sp2) bonds DOI
Lei Wan,

Yi-Zhou Tong,

Xi Lu

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(7), P. 109283 - 109283

Published: Nov. 9, 2023

Language: Английский

Citations

8
Ni/Photoredox-catalyzed coupling of aryl bromides and methylenecyclopropanes via selective distal bond cleavage DOI

Ben Mao,

Min Shi, Yin Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5033 - 5043

Published: Jan. 1, 2024

A series of 1,1-dibenzylethylene derivatives were obtained in moderate-to-good yields via double coupling aryl bromides and methylenecyclopropanes Ni/photoredox catalysis. The critical roles nickel this reaction disclosed.

Language: Английский

Citations

2
Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates DOI

Liang Zou,

Huimin Yang, Tian Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15822 - 15833

Published: Oct. 18, 2024

Herein, we report a general and efficient Ni-catalyzed reductive cross-coupling reaction of substituted vinyl bromides α-chloro phosphonates to access set α-vinyl using zinc as the terminal reductant. This exhibits broad substrate adaptability good functional group tolerance, which allows afford diverse compounds including structurally complex motifs from natural products drugs. Furthermore, practicality was certificated through gram-scale transformation experiments. The preliminary mechanistic investigations support radical chain process. potential realize enantiomeric control makes it more valuable for further exploration.

Language: Английский

Citations

0