Aerobic Oxidative Functionalization of Indoles

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(18), С. 3795 - 3823

Опубликована: Май 18, 2020

Abstract The synthetic methodology for direct indole functionalizations is of great significance in chemistry and has been intensively investigated the last few decades. From perspective green chemistry, oxygen best choice as terminal oxidant molecular synthesis. Hence, aerobic oxidative functionalization indoles became a hot research topic decade. Numerous efficient protocols this field have discovered that enable facile transformations to related valuable compounds, which are summarized discussed detail review. magnified image

Язык: Английский

---

Is Cu(iii) a necessary intermediate in Cu-mediated coupling reactions? A mechanistic point of view

Chemical Communications, Год журнала: 2020, Номер 56(49), С. 6609 - 6619

Опубликована: Янв. 1, 2020

The mechanism of copper-mediated coupling reactions has aroused widespread interest, and it been found to not be as simple initially thought. In this article, we give an overview the recent advances in field. Notably, focus on whether presence CuIII is adopted catalytic cycle. Attention paid key CuII species, which can generated by radical-type or single electron transfer (SET) oxidation CuI. species oxidized SET using a nucleophilic radical for further reductive elimination. Alternatively, substitution bimetallic elimination avoid formation CuIII, also achieved.

Язык: Английский

---

Metal-free synthesis of indolo[2,3-b]indoles through aerobic cascade dehydrogenative aromatization/oxidative annulation

Green Synthesis and Catalysis, Год журнала: 2021, Номер 2(1), С. 78 - 81

Опубликована: Янв. 22, 2021

A convenient method for the rapid construction of indolo[2,3-b]indoles has been developed. This cascade reaction involving condensation, dehydroaromatization, and oxidative annulation was achieved in a one-pot TMSI/DMSO system, providing diversity functionalized satisfactory yields under facile metal-free conditions. The present protocol provides straightforward approach to access structurally valuable indolo[2,3-b], indoles.

Язык: Английский

---

One-electron oxidative dehydrogenative annulation and cyclization reactions

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(15), С. 2107 - 2144

Опубликована: Янв. 1, 2020

This review focuses on the recent advances in one-electron oxidation involved oxidative dehydrogenative annulations and cyclizations for intermolecular intramolecular construction of valuable ring structures.

Язык: Английский

---

Copper–iodine co-catalyzed C–H aminoalkenylation of indoles via temperature-controlled selectivity switch: facile synthesis of 2-azolyl-3-alkenylindoles

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(14), С. 3794 - 3799

Опубликована: Янв. 1, 2022

An efficient copper–iodine co-catalyzed 2,3-difunctionalization of indoles with azoles and phenols via temperature-controlled selectivity switch has been developed for the green synthesis 2-azolyl-3-alkenylindoles.

Язык: Английский

---

Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(16), С. 10967 - 10981

Опубликована: Июль 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Язык: Английский

---

Iron–iodine co-catalysis towards tandem C–N/C–C bond formation: one-pot regioselective synthesis of 2-amino-3-alkylindoles

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(22), С. 6165 - 6171

Опубликована: Янв. 1, 2022

An efficient intermolecular C2,3-H aminoalkylation of indoles with 9 H -xanthenes and azoles via iron–iodine co-catalyzed tandem C–N/C–C bond formation has been developed.

Язык: Английский

---

Synthesis of 2,3‐Diaminoindolesvia a Copper‐Iodine Co‐catalytic Strategy

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(24), С. 3567 - 3572

Опубликована: Авг. 28, 2023

Comprehensive Summary A one‐pot synthesis of vicinal diamines using indoles, azoles and phenothiazines in a tandem multi‐component reaction is developed. The utilization copper‐iodine co‐catalytic system enables the generation diverse range diaminoindoles with good selectivity moderate to yields. An attractive aspect this method that it can be conducted under mild environmentally friendly conditions, showcasing its potential as an alternative approach for synthesizing diamines. Moreover, use multicomponent highlights power versatility such strategies synthetic chemistry.

Язык: Английский

---

Iridium/Acid Cocatalyzed Direct Access to Fused Indoles via Transfer Hydrogenative Annulation of Quinolines and 1,2-Diketones

Organic Letters, Год журнала: 2020, Номер 22(6), С. 2308 - 2312

Опубликована: Фев. 28, 2020

Herein, we present an unprecedented iridium/acid cocatalyzed construction of fused indoles via transfer hydrogenative annulation nonactivated quinolines and 1,2-diketones. The products are assembled initial reduction followed by selective coupling 1,2-diketones with the N C8 sites quinolyl skeleton. developed synthetic method features operational simplicity, readily available feedstocks, applicability for streamline synthesis functional molecules, high step atom efficiency, generation water as byproduct.

Язык: Английский

---

Visible‐Light‐Induced Aerobic Intramolecular Cyclization of (2‐Aminophenyl)(1H‐indol‐1‐yl)methanones: Direct Access to Bioactive Tryptanthrin and its Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1654 - 1659

Опубликована: Май 1, 2023

Abstract Visible‐light‐induced mild, transition metal, base, and photocatalyst‐free green protocol has been developed for the synthesis of tryptanthrin its derivatives. The present reaction is compatible with a wide range substrates good to high yields. Further, novel synthetic transformation derivatives achieved by decarboxylative addition cyanoacetic acid first time. This proceeds visible‐light‐induced single electron transfer between substrate oxygen, followed intramolecular cyclization without use an external photocatalyst. magnified image

Язык: Английский

---