General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides DOI Creative Commons
Roberto del Río‐Rodríguez,

Lorena Fragoso-Jarillo,

Alberto F. Garrido‐Castro

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(22), P. 6512 - 6518

Published: Jan. 1, 2022

Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of

Language: Английский

Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1H)-ones with N-hydroxyphthalimide esters DOI
Kaikai Niu,

Lingyun Song,

Yanke Hao

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(78), P. 11673 - 11676

Published: Jan. 1, 2020

Electrochemical decarboxylative C3 alkylation of a wide range quinoxalin-2(1H)-ones under metal- and additive-free conditions was reported.

Language: Английский

Citations

86

Advances in Electrochemical Decarboxylative Transformation Reactions DOI
Velayudham Ramadoss, Yue Zheng,

Xiaoqing Shao

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(10), P. 3213 - 3228

Published: July 7, 2020

Abstract Owing to their non‐toxic, stable, inexpensive properties, carboxylic acids are considered as environmentally benign alternatives coupling partners in various organic transformations. Electrochemical mediated decarboxylation of acid has emerged a new and efficient methodology for the construction carbon‐carbon or carbon‐heteroatom bonds. Compared with transition‐metal catalysis photoredox catalysis, electro‐organic decarboxylative transformations green sustainable protocol due absence chemical oxidants strong bases. Further, it exhibits good tolerance functional groups. In this Minireview, we summarize recent advances discoveries on electrochemical C−C C−heteroatoms bond formations.

Language: Английский

Citations

76

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis DOI
Wenzhao Zhang,

Nianmin Hong,

Song Lu

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2574 - 2584

Published: April 9, 2021

Abstract Electroorganic synthesis has recently become a rapidly blossoming research area within the organic community. It should be noted that electrochemical reaction is always balanced system with two half‐cell reactions‐oxidation and reduction. Most strategies, however, typically focus on one of sides for desired transformations. Paired electrolysis desirable half reactions running simultaneously, thus maximizing overall margin atom energy economy. Meanwhile, spatial separation between oxidation reduction essential feature electrochemistry, offering unique opportunities development redox‐neutral would otherwise challenging to accomplish in conventional flask setting. This review discusses most recent illustrative examples paired special emphasis sequential convergent processes.

Language: Английский

Citations

66

Recent progress on electrochemical synthesis involving carboxylic acids DOI

Na Chen,

Zenghui Ye, Fengzhi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(25), P. 5501 - 5520

Published: Jan. 1, 2021

Recent progress on sustainable electrochemical synthesis involving carboxylic acids was reviewed.

Language: Английский

Citations

57

Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides DOI

Rupashri Dash,

Satya Prakash Panda,

Kuldeep Singh Bhati

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7227 - 7232

Published: Aug. 20, 2024

We present an electrochemical alkylation of azauracils using N-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several are shown to undergo with array NHPI esters (1°, 2°, 3°, sterically congested), providing the desired products in good excellent yields. This operationally simple method is robust, scalable, suitable for both batch flow setups.

Language: Английский

Citations

9

Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis DOI Creative Commons

Yun-Zhao Wang,

Bing Sun, Jianfeng Guo

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 28, 2025

Abstract Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling benzyl chlorides aryl halides, yielding chiral 1,1-diaryl compounds good to excellent enantioselectivity. This catalytic reaction can not only be applied chlorides/bromides, which are challenging access other means, but also containing silicon groups. Additionally, absence sacrificial anode lays foundation for scalability. The combination cyclic voltammetry analysis electrode potential studies suggests that Ni I species activate halides via oxidative addition and alkyl single electron transfer.

Language: Английский

Citations

1

Photo-Induced Cross-Dehydrogenative Alkylation of Heteroarenes with Alkanes under Aerobic Conditions DOI
Jun Xu,

Heng Cai,

Jiabin Shen

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(24), P. 17816 - 17832

Published: Dec. 7, 2021

We report a Minisci-type cross-dehydrogenative alkylation in an aerobic atmosphere using abundant and inexpensive cerium chloride as photocatalyst air oxidant. This photoreaction exhibits excellent tolerance to functional groups is suitable for both heteroarene alkane substrates under mild conditions, generating the corresponding products moderate-to-good yields. Our method provides alternative approach late-stage functionalization of valuable substrates.

Language: Английский

Citations

52

Recent Advances in C(sp3)–C(sp3) and C(sp3)–C(sp2) Bond Formation through Cathodic Reactions: Reductive and Convergent Paired Electrolyses DOI Creative Commons
Aurélie Claraz, Géraldine Masson

ACS Organic & Inorganic Au, Journal Year: 2021, Volume and Issue: 2(2), P. 126 - 147

Published: Dec. 22, 2021

The formation of C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds is one the major research goals synthetic chemists. Electrochemistry commonly considered to be an appealing means drive redox reactions in a safe sustainable fashion has been utilized for C–C bond-forming reactions. Compared anodic oxidative methods, which have extensively explored, cathodic processes are much less investigated, whereas it can pave way alternative retrosynthetic disconnections target molecules discovery new transformations. This review provides overview on recent achievements construction via since 2017. It includes electrochemical reductions convergent paired electrolyses.

Language: Английский

Citations

51

Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins with unactivated alkyl iodides DOI

Jun Sun,

Hua Yang, Bo Zhang

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 24(2), P. 858 - 863

Published: Dec. 13, 2021

A visible-light-mediated direct C3-alkylation of quinoxalin-2(1 H )-ones and coumarins with unactivated alkyl iodides under metal- external photocatalyst-free conditions is described.

Language: Английский

Citations

46

Visible‐Light‐Promoted Electron Donor‐Acceptor Complex Enabled Decarboxylative Alkylation of Quinoxalin‐2(1H)‐ones and N‐Hydroxyphthalimide Esters with Na2S as a Catalytic Donor DOI

Hai‐Yang Song,

Zhuo‐Tao Zhang,

Hong‐Yu Tan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(2)

Published: Jan. 11, 2023

Abstract We developed a novel and efficient method for the synthesis of various 3‐alkylated quinoxalin‐2(1 H )‐ones (32 examples, 70%–96% yields) through electron donor‐acceptor complex enabled alkylation with N ‐ hydroxyphthalimide esters as alkyl source Na 2 S catalytic donor under external photocatalyst‐, oxidant‐ additive‐free conditions.

Language: Английский

Citations

22