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

Electrochemical C−H deuteration of pyridine derivatives with D2O DOI Creative Commons
Zhiwei Zhao,

Ranran Zhang,

Yaowen Liu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 7, 2024

Herein, we develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C - H deuteration of pyridine derivatives with economic convenient D

Language: Английский

Citations

16
Reductive alkyl-alkyl coupling from isolable nickel-alkyl complexes DOI
Samir Al Zubaydi,

Shivam Waske,

Volkan Akyildiz

et al.

Nature, Journal Year: 2024, Volume and Issue: 634(8034), P. 585 - 591

Published: Aug. 29, 2024

Language: Английский

Citations

10
Organo-mediator enabled electrochemical transformations DOI
Wei-Mei Zeng, Yanwei Wang,

Chunhui Peng

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review highlights organo-mediators that enable electrochemical reactions via outer-sphere electron transfer (ET), offering advantages such as availability, tunability, and simplified post-processing compared to direct electrolysis.

Language: Английский

Citations

1
Electrochemical conversion of organic compounds and inorganic small molecules DOI

Wei-Mei Zeng,

Youai Qiu

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 3223 - 3246

Published: July 9, 2024

Language: Английский

Citations

7
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

7
Electrochemical Glycosylation via Halogen-Atom-Transfer for C-Glycoside Assembly DOI Creative Commons
Jun Wu, Purushothaman Rajeshwaran,

Felix Kallert

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11532 - 11544

Published: July 19, 2024

Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide activations via halogen-atom transfer and C-glycosylation. The radical addition to alkenes led C-alkyl glycoside synthesis under precious metal-free reaction conditions from readily available bromides. robustness of our e-XAT strategy was further mirrored by C-aryl C-acyl glycosides assembly through nickela-electrocatalysis. Our approach provides orthogonal with expedient scope, hence representing a general method direct C-glycosides assembly.

Language: Английский

Citations

6
Organo-electroreduction enables arylcarboxylation of styrenes DOI
Yanwei Wang, Qian Wang, Zile Zhu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

Language: Английский

Citations

6
A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis DOI Creative Commons
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2500 - 2566

Published: Oct. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Language: Английский

Citations

6
Iron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers DOI
Andria L. Pace,

Felix Xu,

Wei Liu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

Quaternary carbon centers are desirable targets for drug discovery and complex molecule synthesis, yet the synthesis of these motifs within traditional cross-coupling paradigms remains a significant challenge due to competing β-hydride elimination pathways. In contrast, bimolecular homolytic substitution (SH2) mechanism offers unique attractive alternative pathway. Metal porphyrin complexes have emerged as privileged catalysts owing their ability selectively form primary metal–alkyl complexes, thereby eliminating challenges associated with tertiary alkyl complexation metal center. Herein, we report an iron-catalyzed cross-electrophile coupling bromides electrophiles formation all-carbon quaternary through biomimetic SH2 mechanism.

Language: Английский

Citations

4
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