Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis DOI Creative Commons
Xiangzhang Tao, Wooseok Lee,

Zhimin Xu

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(47)

Published: Nov. 22, 2024

We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp 3 )–C(sp ) and 2 bonds from readily available alkyl bistriflimides. This methodology involves assembly two leaving groups on amines to form bistriflimides, followed by their effective coupling with wide range halides, pseudohalides, aryl alkenyl halides under electrochemical reductive conditions. Moreover, successful application relay transition metal–free cross-electrophile further demonstrates versatility bistriflimides as valuable building blocks in organic synthesis. Combined control experiments density functional theory calculations provide insights into reaction pathway crucial role iodide catalytic process.

Language: Английский

Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis DOI Creative Commons
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Language: Английский

Citations

18
Bis(pinacolato)diboron‐Enabled Ni‐Catalyzed Reductive Arylation/Vinylation of Alkyl Electrophiles DOI Creative Commons
Deli Sun, Yuxin Gong,

Yu Wu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(31)

Published: June 17, 2024

Abstract Herein, the use of economically and environmentally friendly bis(pinacolato)diboron (B 2 Pin ) is described as a non‐metallic reductant in mediating Ni‐catalyzed C(sp 3 )–C(sp reductive cross‐coupling alkyl electrophiles with aryl/vinyl halides. This method exhibits excellent suitability for heteroaryl halides halides/Katritzky salts. The present study compatible an situ halogenation alcohol method, allowing selective mono‐functionalization diols bio‐relevant alcohols (e.g., carbohydrates). B shows potential easy scalability without introducing additional metal impurities into products. It observed first time realm cross‐electrophile coupling chemistry that can sever to reduce Ni II 0 . mechanistic insight may inspire development new bond‐forming methodologies otherwise be difficult achieve reductant.

Language: Английский

Citations

4
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
Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis DOI Creative Commons
Xiangzhang Tao, Wooseok Lee,

Zhimin Xu

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(47)

Published: Nov. 22, 2024

We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp 3 )–C(sp ) and 2 bonds from readily available alkyl bistriflimides. This methodology involves assembly two leaving groups on amines to form bistriflimides, followed by their effective coupling with wide range halides, pseudohalides, aryl alkenyl halides under electrochemical reductive conditions. Moreover, successful application relay transition metal–free cross-electrophile further demonstrates versatility bistriflimides as valuable building blocks in organic synthesis. Combined control experiments density functional theory calculations provide insights into reaction pathway crucial role iodide catalytic process.

Language: Английский

Citations

0