Cross‐Electrophile Couplings (XECs) between Similar Electrophile Reagents DOI
Jie Lei, Shan Yu, Zhigang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(24), P. 3518 - 3532

Published: Nov. 1, 2024

Comprehensive Summary Cross‐electrophile couplings (XEC), a crucial subset of cross‐coupling reactions, center on the formation robust C—C bonds through union two electrophiles. Usually, such reactions have primarily been catalyzed by transition metals. However, with steady advancements in photochemical and electrochemical technologies, XEC significantly progressed broadened their scope, allowing for utilization wider array tolerable functional groups, thus revealing vast application prospects. This review aims to systematically summarize current prevalent types electrophiles delve into specific examples within involving identical groups. Specifically, XECs between same type halides received considerable attention, whereas carboxylic acids alcohols are still early stages investigation. Furthermore, certain other common remain unexplored this context. Moreover, underscores remarkable contributions photochemistry electrochemistry field aiming provide valuable insights inspiration researchers. Also, hopes spark further interest thereby fueling continuous development advancement exciting area research. Key Scientists Since 1960s, reaction substantial, driven metal catalysts. In area, many distinguished scientists contributed wisdom efforts. Particularly noteworthy is that, during systematic study 2016, MacMillan achieved photocatalytic aryl bromides alkyl bromides; 2020, Weix successfully realized nickel‐catalyzed chlorides chlorides. Concurrently, from researchers as Mei, Wolf, Sevov, Lin, Shen, Browne, Zhang, Qiu expanded scope various halides. By 2022, Baran significant milestone acids, broadening research area. noted, including Weix, Lian, Tu, Stahl conducting pioneering work executing protective It foreseen that ongoing endeavors will concentrate expansion diverse

Language: Английский

Flow Electroreductive Nickel‐Catalyzed Cyclopropanation of Alkenes Using gem‐Dichloroalkanes DOI Creative Commons
Morgan Regnier, Clara Vega, Dimitris I. Ioannou

et al.

Angewandte Chemie International Edition, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Abstract Cyclopropanes are valuable motifs in organic synthesis, widely featured pharmaceuticals and functional materials. Herein, we report an efficient electrochemical methodology for the cyclopropanation of alkenes, leveraging a nickel‐catalyzed process continuous‐flow. The developed protocol demonstrates broad substrate scope, accommodating both electron‐rich electron‐poor alkenes with high group tolerance. Beyond dichloromethane as feedstock methylene source, enables synthesis methylated, deuterated, chloro‐substituted cyclopropanes. Mechanistic investigations suggest electro‐generation nickel carbene key intermediate. Notably, reaction operates under ambient conditions, tolerates air moisture, achieves scalability through continuous‐flow technology, offering straightforward route to multi‐gram quantities enhanced throughput.

Language: Английский

Citations

1
Electrochemical Cyclopropanation of 1,3-Dialkyl Bromides DOI
Sylvain Charvet, Clément Jacob,

Aurore Dietsch

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(11), P. 4011 - 4017

Published: Oct. 22, 2024

An electrochemical synthesis of mono- and 1,1-disubstituted cyclopropanes is demonstrated. Starting from readily available 1,3-dialkyl bromides, this method hinges on the integration a sacrificial reductant alongside cost-effective cathode anode materials. The refined approach eliminates necessity for divided cell use hazardous or costly electrodes, thereby streamlining transition protocol to continuous flow system. In addition, an alternative that utilizes simple also described.

Language: Английский

Citations

1
Cross‐Electrophile Couplings (XECs) between Similar Electrophile Reagents DOI
Jie Lei, Shan Yu, Zhigang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(24), P. 3518 - 3532

Published: Nov. 1, 2024

Comprehensive Summary Cross‐electrophile couplings (XEC), a crucial subset of cross‐coupling reactions, center on the formation robust C—C bonds through union two electrophiles. Usually, such reactions have primarily been catalyzed by transition metals. However, with steady advancements in photochemical and electrochemical technologies, XEC significantly progressed broadened their scope, allowing for utilization wider array tolerable functional groups, thus revealing vast application prospects. This review aims to systematically summarize current prevalent types electrophiles delve into specific examples within involving identical groups. Specifically, XECs between same type halides received considerable attention, whereas carboxylic acids alcohols are still early stages investigation. Furthermore, certain other common remain unexplored this context. Moreover, underscores remarkable contributions photochemistry electrochemistry field aiming provide valuable insights inspiration researchers. Also, hopes spark further interest thereby fueling continuous development advancement exciting area research. Key Scientists Since 1960s, reaction substantial, driven metal catalysts. In area, many distinguished scientists contributed wisdom efforts. Particularly noteworthy is that, during systematic study 2016, MacMillan achieved photocatalytic aryl bromides alkyl bromides; 2020, Weix successfully realized nickel‐catalyzed chlorides chlorides. Concurrently, from researchers as Mei, Wolf, Sevov, Lin, Shen, Browne, Zhang, Qiu expanded scope various halides. By 2022, Baran significant milestone acids, broadening research area. noted, including Weix, Lian, Tu, Stahl conducting pioneering work executing protective It foreseen that ongoing endeavors will concentrate expansion diverse

Language: Английский

Citations

1