Strongly Reducing Helical Phenothiazines as Recyclable Organophotoredox Catalysts DOI Creative Commons

Haru Ando,

Hiroyoshi Takamura,

Isao Kadota

и другие.

Опубликована: Ноя. 15, 2023

Photocatalysts have recently attracted significant interest due to their potential applications in sustainable energy-conversion systems. In organic chemistry, recyclability of photocatalysts are important characteristics with respect environmental concerns and economic benefits. Metal-based polypyridyl complexes ruthenium iridium been widely used as recyclable homogeneous photoredox catalysts, whereas organophotoredox catalysts less explored usually limited the use polymer methods. Herein, we report design synthesis phenothiazine (PTHS 1–3). These exhibit relatively high excited-state oxidation potentials (E1/2ox* = −2.34 −2.40 V vs. SCE) that can efficiently promote reactions via one-electron reduction 1,3-bis(trifluoromethyl)benzene 4-trifluoromethyliodobenzene, which (Ep/2 −2.07 −2.16 SCE). Notably, when recycling performance was evaluated cross-coupling reaction between an aryl halide triethylphosphite, PTHS-1 be recovered at least four times without loss its catalytic activity. The present reusable thus represent a promising tool for synthesis.

Язык: Английский

Water-promoted defluorinative synthesis of fluoroalkylated 1,5-diazapentadienes by using (NH4)2CO3 as an NH2 and NH source DOI
Wei Han, Yulan Chen,

Xi Tang

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(23), С. 9672 - 9679

Опубликована: Янв. 1, 2023

A H 2 O-promoted and (NH 4 ) CO 3 -enabled defluoroiminization reaction of fluoroalkyl alkenes for the synthesis fluoroalkylated 1,5-diazapentadienes has been developed.

Язык: Английский

Процитировано

17

Base-Promoted [5 + 1 + 3] Cascade Cyclization of o-Nitrochalcones, Elemental Sulfur, and Guanidine to Benzo[4,5]thieno[3,2-d]pyrimidine Frameworks DOI
Juan Wan,

Shuntao Huang,

Zhou Zhang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(24), С. 4451 - 4455

Опубликована: Июнь 9, 2023

An unexpected [5 + 1 3] cascade cyclization to the preparation of benzo[4,5]thieno[3,2-d]pyrimidine derivatives has been disclosed. In new protocol, o-nitrochalcones reacted with elemental sulfur and guanidine promoted by NaOH, which in EtOH for 20 min, providing structurally diverse benzo[4,5]thieno[3,2-d]pyrimidines good yields (77-89%) wide substrate compatibility (33 examples).

Язык: Английский

Процитировано

15

Strongly reducing helical phenothiazines as recyclable organophotoredox catalysts DOI Creative Commons

Haru Ando,

Hiroyoshi Takamura,

Isao Kadota

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(36), С. 4765 - 4768

Опубликована: Янв. 1, 2024

Recyclable phenothiazine organophotoredox catalysts (PTHS 1–3, E 1/2 ox * = −2.34 to −2.40 V vs. SCE) have been developed.

Язык: Английский

Процитировано

6

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH4I-Promoted Three-Component Tandem Reaction DOI
Fang Fang, Jie Xia,

Siying Quan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14697 - 14707

Опубликована: Сен. 29, 2023

A facile and practical approach for the preparation of substituted pyrimidines from ketones, NH4OAc, N,N-dimethylformamide dimethyl acetal has been described. This NH4I-promoted three-component tandem reaction affords a broad range in acceptable yields under metal- solvent-free conditions. The present methodology features advantages simple easily available starting materials, conditions, substrate scope with good functional group tolerance, gram-scale synthesis.

Язык: Английский

Процитировано

10

Visible‐Light‐Promoted Cascade Coupling of 2‐Isocyanonaphthalenes with Elemental Sulfur and Amines to Construct Naphtho[2,1‐d]thiazol‐2‐Amines DOI

Hongyu Ding,

Siyu Shi, Yanan Hou

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(27)

Опубликована: Март 11, 2024

A visible-light-induced strategy has been explored for the synthesis of naphtho[2,1-d]thiazol-2-amines through ortho-C-H sulfuration 2-isocyanonaphthalenes with elemental sulfur and amines under external photocatalyst-free conditions. This three-component reaction, which utilizes as odorless source, molecular oxygen clean oxidant, visible light energy provides a mild efficient approach to construct series naphtho[2,1-d]thiazol-2-amines. Preliminary mechanistic studies indicated that visible-light-promoted photoexcitation reaction intermediates consisting thioureas DBU might be involved in this transformation.

Язык: Английский

Процитировано

2

Iodine-Catalyzed Cyclization of o-Nitrothiophenols with Cyclohexanones to Phenothiazines DOI

Yinglin Zhao,

Jin Zhang,

Jingwu Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7478 - 7484

Опубликована: Май 22, 2024

Here, a novel iodine-catalyzed direct cyclization of

Язык: Английский

Процитировано

2

Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature DOI
Bin Tan,

Zhuoqin Li,

Xinlin Zhou

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4779 - 4784

Опубликована: Янв. 1, 2024

A novel and unique nitrogen atom insertion into naphthoquinone rings to construct structurally valuable polycyclic heterocycles at room temperature under transition-metal-free conditions has been described.

Язык: Английский

Процитировано

2

Chemoselective three-component synthesis of α-carbolines under metal-free conditions DOI
Wei Feng, Chao Zhang, Xinlin Zhou

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(21), С. 5457 - 5462

Опубликована: Янв. 1, 2023

An I 2 O 5 -promoted chemoselective three-component tandem reaction of indole-3-carboxaldehydes, ammonium acetate, and alkynes for the construction α-carbolines under metal-free conditions has been described.

Язык: Английский

Процитировано

5

Metal‐Free Synthesis of 2‐Aminobenzothiazoles via I2‐Catalyzed Tandem Cyclization Reaction of Amines and Carbon Disulfide DOI
Ting Chen, Wei Feng, Ruitong Yang

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(8), С. 846 - 852

Опубликована: Дек. 20, 2023

Comprehensive Summary A convenient approach for the construction of 2‐aminobenzothiazoles via I 2 ‐catalyzed tandem cyclization reaction amines and carbon disulfide has been developed. The present starts from simple readily available starting materials, affording a series in up to 89% yields under metal‐free conditions. In this work, C—H/N—H functionalization was achieved multiple C‐hetero bonds were successfully constructed one pot.

Язык: Английский

Процитировано

5

Regioselective synthesis of indazolo[2,3-a]quinazolines enabled by I2/S-facilitated annulation relay dehydrogenative aromatization of cyclohexanones DOI
Qinghe Gao,

Yimei Guo,

Penghui Cao

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(93), С. 13835 - 13838

Опубликована: Янв. 1, 2023

A method for concise and regioselective synthesis of indazolo[2,3- a ]quinazolines has been developed via sequential annulation dehydrogenative aromatization cyclohexanones.

Язык: Английский

Процитировано

4