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

12
Electroreductive Cross-Coupling Reactions: Carboxylation, Deuteration, and Alkylation DOI
Pengfei Li, Yanwei Wang, Hanying Zhao

et al.

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

ConspectusElectrochemistry has been used as a tool to drive chemical reactions for more than two centuries. With the help of an electrode and power source, chemists are provided with system whose potential can be precisely dialed in. The theoretically infinite redox range renders electrochemistry capable oxidizing or reducing some most tenacious compounds. Indeed, electroreduction offers alternative generating highly active intermediates from electrophiles (e.g., halides, alkenes, etc.) in organic synthesis, which untouchable traditional reduction methods. Meanwhile, reductive coupling extensively utilized both industrial academic settings due their ability swiftly, accurately, effectively construct C–C C–X bonds, present innovative approaches synthesizing complex molecules. Nonetheless, its application is constrained by several inherent limitations: (a) requirement stoichiometric quantities agents, (b) scarce activation strategies inert substrates high potentials, (c) incomplete mechanistic elucidation, (d) challenges isolation intermediates. merging represents attractive approach address above limitations synthesis seen increasing use synthetic community over past few years.Since 2020, our group dedicated developing electroreductive cross-coupling using readily available small molecules, such arenes, CO2, D2O, value-added products. Electroreductive chemistry versatile powerful capacity precise selectivity control, allowed us develop three electrochemical modes lab: (1) An economically advantageous direct (EDR) strategy that emphasizes efficiency, achieves atom utilization, minimizes unnecessary atomic waste. (2) A class organo-mediated (EOMR) methods controlling reaction pathways. This allows modulation processes enhance efficiency selectivity. (3) metal-catalyzed (EMCR) method enables selective functionalization specific bonds functional groups under mild conditions, thereby occurrence side reactions. We commenced studies establishing organic-mediator-promoted carboxylation aryl alkyl halides. was then employed arylcarboxylation simple styrenes halides manner. electrolysis arenes epoxides CO2 carboxyl source achieved. Moreover, through adjustment we successfully accomplished deuteration olefins, unactivated enabling efficient formation D-labeled Finally, building on previous understanding developed series alkylation enable C(sp3)–C(sp3)

Language: Английский

Citations

4
Advances in Accessing Rare Oxidation States of Nickel for Catalytic Innovation DOI

Aankhi Khamrai,

Sudipta Kumar Ghosh, Venkataraman Ganesh

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Nickel catalysis has experienced a renaissance over the past two decades, driven by its ability to access diverse oxidation states (0 +4). This review consolidates advancements in nickel chemistry at various states.

Language: Английский

Citations

0
Dearomative Alkylation of Heteroarenium Salts via Blue Light Enabled Homolytic C–C Bond Cleavage DOI

Agshin Garayev,

Emma E. Drake,

Evangelos Miliordos

et al.

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

Published: Feb. 5, 2025

Alkyl substituted nitrogen heterocycles are important building blocks in drug molecules, agrochemicals, and materials. Herein we report a simple efficient way to prepare such compounds by coupling alkyl halides with heteroarenium salts. Detailed experimental computational studies indicate that this reaction goes through radical avoids the formation of undesired homocoupling salts via recycling dimers C–C bond cleavage under blue light.

Language: Английский

Citations

0
Sulfonyl hydrazides as a general redox-neutral platform for radical cross-coupling DOI

Jiawei Sun,

Áron Péter,

Jiayan He

et al.

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

Published: March 6, 2025

Language: Английский

Citations

0
Nickel-mediated aerobic Csp–nucleophile coupling DOI
D. Das, Long P. Dinh,

Ryan E. Smith

et al.

Trends in Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0
Photoinduced pinacol coupling of carbon-carbon bonds via triethoxysilane or Hantzsch Ester DOI
Jianhua Liu,

Gelan Wang,

Chen Chen

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115088 - 115088

Published: April 5, 2025

Language: Английский

Citations

0
Reaction for coupling 3D molecular fragments expands the chemist’s toolkit DOI

Jonathan Sorbie,

Tianning Diao

Nature, Journal Year: 2024, Volume and Issue: 634(8034), P. 551 - 553

Published: Oct. 9, 2024

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