Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Liu, Qiang; Li, Yanan; Zhang, Huihui; Chen, Bin; Tung, Chen‐Ho; Wu, Li‐Zhu

doi:10.1002/chem.201102299

Cited by 266 publications

(111 citation statements)

References 38 publications

Supporting

Mentioning

100

Contrasting

Unclassified

Order By: Relevance

“…In the initial report by Stephenson, the resultant electrophilic iminium ions were trapped with nitroalkanes to deliver the corresponding α-functionalized products. This strategy has proven general for a wide range of nucleophilic coupling partners including malonates, 21 cyanide, 22 trifluoromethyl anion, 22 electron-rich aromatics, 23 and phosphonates 24 in addition to tethered amines and alcohols which forge the corresponding heterocycles via intramolecular cyclization 25 (Scheme 3). …”

Section: Amine α-Functionalizationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

View full text Add to dashboard Cite

In recent years, photoredox catalysis has come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In a general sense, these approaches rely on the ability of metal complexes and organic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates, thereby generating reactive intermediates. In this Perspective, we highlight the unique ability of photoredox catalysis to expedite the development of completely new reaction mechanisms, with particular emphasis placed on multicatalytic strategies that enable the construction of challenging carbon–carbon and carbon–heteroatom bonds.

show abstract

Section: Amine α-Functionalizationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

View full text Add to dashboard Cite

show abstract

“…The reductive quenching pathway of eosin Y, which operates in the photooxidation of isoquinolines [9], has been studied in a single report [22]. To the best of our knowledge, related data have not been collected for the much more widely used oxidative quenching.…”

Section: Introductionmentioning

confidence: 99%

On the mechanism of photocatalytic reactions with eosin Y

Májek

Filace

Wangelin

2014

Beilstein J. Org. Chem.

259

170

View full text Add to dashboard Cite

SummaryA combined spectroscopic, synthetic, and apparative study has allowed a more detailed mechanistic rationalization of several recently reported eosin Y-catalyzed aromatic substitutions at arenediazonium salts. The operation of rapid acid–base equilibria, direct photolysis pathways, and radical chain reactions has been discussed on the basis of pH, solvent polarity, lamp type, absorption properties, and quantum yields. Determination of the latter proved to be an especially valuable tool for the distinction between radical chain and photocatalytic reactions.

show abstract

“…6,11−15 Conventional triplet photosensitizers are limited to porphyrin derivatives (including Zn(II), Pt(II), or Pd(II) complexes) 16−19 and halogenated xanthane dyes, such as Rose Bangle or Methylene blue, 6,20 as well as some ketone compounds, such as benzophenone, diacetyl, ketocoumarin, etc. 6,21,22 Transitionmetal complexes such as Pt(II), Ir(III), and Ru(II) complexes have also been used as triplet photosensitizers.…”

Section: Introductionmentioning

confidence: 99%

DiiodoBodipy-Perylenebisimide Dyad/Triad: Preparation and Study of the Intramolecular and Intermolecular Electron/Energy Transfer

Mahmood

Küçüköz³

et al. 2015

J. Org. Chem.

View full text Add to dashboard Cite

2,6-diiodoBodipy-perylenebisimide (PBI) dyad and triad were prepared, with the iodoBodipy moiety as the singlet/triplet energy donor and the PBI moiety as the singlet/triplet energy acceptor. IodoBodipy undergoes intersystem crossing (ISC), but PBI is devoid of ISC, and a competition of intramolecular resonance energy transfer (RET) with ISC of the diiodoBodipy moiety is established. The photophysical properties of the compounds were studied with steady-state and femtosecond/nanosecond transient absorption and emission spectroscopy. RET and photoinduced electron transfer (PET) were confirmed. The production of the triplet state is high for the iodinated dyad and the triad (singlet oxygen quantum yield ΦΔ = 80%). The Gibbs free energy changes of the electron transfer (ΔGCS) and the energy level of the charge transfer state (CTS) were analyzed. With nanosecond transient absorption spectroscopy, we confirmed that the triplet state is localized on the PBI moiety in the iodinated dyad and the triad. An exceptionally long lived triplet excited state was observed (τT = 150 μs) for PBI. With the uniodinated reference dyad and triad, we demonstrated that the triplet state localized on the PBI moiety in the iodinated dyad and triad is not produced by charge recombination. These information are useful for the design and study of the fundamental photochemistry of multichromophore organic triplet photosensitizers.

show abstract

Reactivity and Mechanistic Insight into Visible‐Light‐Induced Aerobic Cross‐Dehydrogenative Coupling Reaction by Organophotocatalysts

Cited by 266 publications

References 38 publications

Photoredox Catalysis in Organic Chemistry

Photoredox Catalysis in Organic Chemistry

On the mechanism of photocatalytic reactions with eosin Y

DiiodoBodipy-Perylenebisimide Dyad/Triad: Preparation and Study of the Intramolecular and Intermolecular Electron/Energy Transfer

Contact Info

Product

Resources

About