Controllable Pyridine N-Oxidation–Nucleophilic Dechlorination Process for Enhanced Dechlorination of Chloropyridines: The Cooperation of HCO4 and HO2 DOI
Ying Chen, Lei Tian, Wen Liu

и другие.

Environmental Science & Technology, Год журнала: 2024, Номер unknown

Опубликована: Фев. 8, 2024

Dechlorination of chloropyridines can eliminate their detrimental environmental effects. However, traditional dechlorination technology cannot efficiently break the C–Cl bond chloropyridines, which is restricted by uncontrollable nonselective species. Hence, we propose carbonate species-activated hydrogen peroxide (carbonate species/H2O2) process wherein selective oxidant (peroxymonocarbonate ion, HCO4–) and reductant (hydroperoxide anion, HO2–) controllably coexist manipulation reaction pH. Taking 2-chloropyridine (Cl–Py) as an example, HCO4– first induces Cl–Py into pyridine N-oxidation intermediates, then suffer from nucleophilic HO2–. The obtained efficiencies in species/H2O2 (32.5–84.5%) based on cooperation HO2– are significantly higher than those HO2–-mediated sodium hydroxide/hydrogen (0–43.8%). Theoretical calculations confirm that effectively lower energy barrier process. Moreover, exhibits superior anti-interference performance low electric consumption. Furthermore, completely detoxified via More importantly, applicable for efficient dehalogenation halogenated pyridines pyrazines. This work offers a simple useful strategy to enhance efficiency organics sheds new insights application practical remediation.

Язык: Английский

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

и другие.

Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 450 - 470

Опубликована: Ноя. 3, 2023

Язык: Английский

Процитировано

50

Phenanthroline-Initiated Anti-selective Hydrosulfonylation of Unactivated Alkynes with Sulfonyl Chlorides DOI

Ci-Shuang Dong,

Wen‐Yan Tong,

Peng Ye

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(10), С. 6983 - 6993

Опубликована: Май 8, 2023

A simple and general method for anti-selective hydrosulfonylation of unactivated alkynes with sulfonyl chlorides in the presence a catalytic amount phenanthroline-based Lewis base (Me3Si)3SiH as hydrogen atom donor has been developed. The protocol proceeds efficiently under mild metal-free conditions, delivering diverse set (Z)-vinyl sulfones high stereoselectivity. Additionally, displays excellent functional-group compatibility can be applied to late-stage modifications complex drugs their derivatives. Experimental density functional theory studies unveiled that key transformation's success is employment base, which interacts form halogen-bond accelerates cleavage S–Cl bonds irradiation visible light.

Язык: Английский

Процитировано

27

Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3+OTf) as a Bifunctional Reagent DOI
Xiang Fang,

Dehui Wang,

Kun Xu

и другие.

Organic Letters, Год журнала: 2023, Номер 26(1), С. 411 - 415

Опубликована: Дек. 26, 2023

We report a strategic exploitation of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as both electromediator and CF3 radical precursors for paired electrolysis. Enabled by this strategy, the three-component trifluoromethylheteroaromatization alkenes alkynes was realized. The superiority TT-CF3+OTf– to other electrophilic reagents is attributed cathodic generation thianthrene (TT) mediator, which shifts heterogeneous oxidation interest homogeneous one.

Язык: Английский

Процитировано

26

An electrochemical-enabled cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles DOI
Dandan Li, Long Chen,

Yang Jin

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(12), С. 4656 - 4661

Опубликована: Янв. 1, 2023

An electrochemical-enabled three-component cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles has been developed under external oxidant-free conditions.

Язык: Английский

Процитировано

22

Electrochemical Atom Transfer Radical Addition of Polychloroalkanes to Olefins Promoted by 4,4‐Ditert‐butyl Bipyridine DOI

Fei Lian,

Fei‐Xian Luo, Meng Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(13), С. 1583 - 1588

Опубликована: Фев. 14, 2023

Comprehensive Summary A new electrochemical strategy for the atom transfer radical addition (ATRA) of polychloroalkanes across olefins has been realized by synergism paired electrolysis and halogen bonding activation. Notably, readily accessible 4,4‐di‐ tert ‐butyl bipyridine (dtbpy), acting as a acceptor, shifted reduction potential C—Cl bonds positively 110 mV. The decreased operating leads to wide substrate scope excellent functional group compatibility. diverse array terminal internal alkenes such (hetero)aryl olefins, unactive aliphatic natural products drugs‐derived were well compatible.

Язык: Английский

Процитировано

21

Electrocatalytic C–H/S–H Coupling of Amino Pyrazoles and Thiophenols: Synthesis of Amino Pyrazole Thioether Derivatives DOI
Wenbao Zhang, Q. Zou, Qian Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5434 - 5441

Опубликована: Апрель 6, 2024

A mild method for the C–H/S–H coupling of pyrazol-5-amines and thiophenols was developed via electrochemistry, giving diverse amino pyrazole thioether derivatives in 37–98% yields. This electrochemical reaction is sustainable an atom-efficient approach with good functional group tolerance scalability by avoiding metal external chemical oxidants.

Язык: Английский

Процитировано

5

Divergent synthesis of aryl amines and dihydroquinazolinones via electrochemistry-enabled rhodium-catalyzed C–H functionalization DOI

Yi‐Kang Xing,

Zhenhua Wang, Ping Fang

и другие.

Science China Chemistry, Год журнала: 2023, Номер 66(10), С. 2863 - 2870

Опубликована: Июнь 12, 2023

Язык: Английский

Процитировано

10

Electrosynthesis of Thiocyanated/Iodinated/Brominated Pyrazol‐5‐amines and Thiocyanated Enamines via C(sp2)−H Functionalization DOI
Peng Qian, Siqi Jiang, Wenbao Zhang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1782 - 1787

Опубликована: Май 11, 2023

Abstract An electrochemical method for the C( sp 2 )−H thiocyanation of pyrazol‐5‐amines and enamines were developed in an undivided cell. A variety thiocyanated pyrazol‐5‐amine enamine derivatives accessed 36–91% yields, employing thiocyanate salts as electrolyte thiocyanating reagent. Moreover, this protocol can be extended to synthesis various iodinated brominated 51–95% yields. This does not require a metal or external chemical oxidants tolerates unprotected amino groups.

Язык: Английский

Процитировано

9

Electrophotoredox cerium-catalyzed decarboxylative radical cyclization cascade for the synthesis of alkylated benzimidazo-fused isoquinolinones DOI
Meng Wang,

Dehui Wang,

Kun Xu

и другие.

Catalysis Science & Technology, Год журнала: 2024, Номер 14(4), С. 1037 - 1042

Опубликована: Янв. 1, 2024

We report an electrophotoredox cerium-catalyzed LMCT strategy to incorporate carboxylic acids into radical cyclization cascades. This protocol provides a solution address the challenges in alkylated benzimidazo-fused isoquinolinone synthesis.

Язык: Английский

Процитировано

3

Electrochemically Enable N-Sulfenylation/Phosphinylation of Sulfoximines via Oxidative Dehydrocoupling Reaction DOI
Wenbao Zhang,

Dongsheng Jin,

Yongkang Hu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6106 - 6116

Опубликована: Апрель 18, 2024

An electrochemical oxidative cross-coupling strategy for the synthesis of N-sulfenylsulfoximines from sulfoximines and thiols was accomplished, giving diverse in moderate to good yields. Moreover, this can be extended construct N–P bond N-phosphinylated sulfoximines. With electrons as reagents, dehydrogenation reaction proceeds smoothly absence traditional redox reagents.

Язык: Английский

Процитировано

3