One-electron oxidative dehydrogenative annulation and cyclization reactions

Bao, Xiazhen; Jiang, Wei; Liang, Jia; Huo, Congde

doi:10.1039/d0qo00422g

Cited by 32 publications

(11 citation statements)

References 153 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One strategy for extending conjugation and enhancing the efficiency of luminescence via molecular rigidification is to link arene rings via intramolecular annulation . In this regard, a popular annulation protocol is based on the Scholl reaction (i.e., treatment of polyarenes with p -chloranil or FeCl 3 ), which requires substantial electron density at the arene sites to be linked.…”

Section: Resultsmentioning

confidence: 99%

Tellura(benzo)bithiophenes: Synthesis, Oligomerization, and Phosphorescence

2021

View full text Add to dashboard Cite

A series of planar π-extended Te-containing heteroacenes, termed tellura(benzo)bithiophenes, were synthesized. This new structural class of heterocycle features a tellurophene ring fused to a benzobithiophene unit with aromatic side groups (either −C 6 H 4 i Pr or −C 6 H 4 OCH 3 ) positioned at the 2-and 5-positions of the tellurophene moiety. Although attempts to enhance molecular rigidity and extend ring-framework πdelocalization in a cumenyl (−C 6 H 4 i Pr)-capped tellura(benzo)bithiophene led to oxidation (and Te−C bond scission) to form a diene−one, the formation of an oligomeric tellura(benzo)bithiophene was possible via Kumada catalyst-transfer polycondensation (KCTP). Furthermore, one tellura(benzo)bithiophene derivative exhibits orange-red phosphorescence at room temperature in air when incorporated into a poly(methyl methacrylate) host; accompanying TD-DFT computations provided insight into a potential mechanism for the observed phosphorescence.

show abstract

Section: Resultsmentioning

confidence: 99%

Tellura(benzo)bithiophenes: Synthesis, Oligomerization, and Phosphorescence

2021

View full text Add to dashboard Cite

show abstract

“…In addition to mediating the production of P -center radicals, silver salts are also used to mediate alkyl radicals’ generation via the decarboxylation reaction of alkyl carboxylic acids and are typically accompanied by a one-electron oxidation (OEO) process, which refers to taking an electron away and proceeding with further oxidation. 20 Li's group developed a unique strategy to obtain benzazepin-2-ones in high yields using N -aryl propiolamides and 4-vinyl acids in the presence of silver salts and potassium persulfate (Scheme 4). 21 This developed and promising method possessed the advantages of cheap and accessible K 2 S 2 O 8 as an inorganic oxidant, mild reaction conditions, and good functional group compatibility.…”

Section: Metal-induced Systemmentioning

confidence: 99%

The synthesis of seven- and eight-membered rings by radical strategies

Zhang

Wang

et al. 2022

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

“…The structures of 2a-f were optimized and the required energies were calculated using the Hartree-Fock theory method with the 6-311G(d) basic set. (25), 330 (58), 304 (13), 267 (18), 204 (6), 177 (4), 164 (4), 83 (7), 41 (9) (15), 330 (13), 257 (14), 222 (19), 178 (14), 153 (11), 90 (11) (8), 237 (6), 216 (5), 189 (10), 164 (10), 136 (5), 28 (26)…”

Section: General Informationmentioning

confidence: 99%

“…The advances in photocatalytic oxidative cyclizations catalyzed by titanium dioxide are also known [4]. Oxidative cyclizations occur widely during natural product biosynthesis [5,6] or biomimetic synthesis [7,8]. Thus, oxidative cyclization is one of the most common methods for synthesizing different ring systems.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED

et al. 2022

View full text Add to dashboard Cite

Oxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one of the leading technologies for full-color display panels and eco-friendly lighting sources. In this work, we propose the synthesis of previously unknown benzo[b]chromeno[4,3,2-de][1,6]naphthyridines via intermolecular oxidative cyclization of 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in formic acid. The investigation of the reaction mechanism using 1H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized benzo[b]chromeno[4,3,2-de][1,6]naphthyridines was confirmed by 2D-NMR spectroscopy. Such a rigid geometry of synthesized compounds is desired to minimize non-radiative energy losses in OLEDs. The quantum chemical calculations are also presented in the study.

show abstract

One-electron oxidative dehydrogenative annulation and cyclization reactions

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

Cited by 32 publications

References 153 publications

Tellura(benzo)bithiophenes: Synthesis, Oligomerization, and Phosphorescence

Tellura(benzo)bithiophenes: Synthesis, Oligomerization, and Phosphorescence

The synthesis of seven- and eight-membered rings by radical strategies

Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED

Contact Info

Product

Resources

About