Photochemical Doyle-Kirmse Reaction – a Metal-Free Route to Allenes

10.26434/chemrxiv.10293221 ◽

2019 ◽

Author(s):

katarzyna Orłowska ◽

Katarzyna Rybicka-Jasińska ◽

Piotr Krajewski ◽

Dorota Gryko

Keyword(s):

Blue Light ◽

Sigmatropic Rearrangement ◽

Metal Free ◽

Donor Acceptor ◽

Singlet Carbenes ◽

Sulfonium Ylides

This report describes metal-free, blue light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yields. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.

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Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

10.26434/chemrxiv.11912073 ◽

2020 ◽

Author(s):

José Tiago Menezes Correia ◽

Gustavo Piva da Silva ◽

Camila Menezes Kisukuri ◽

Elias André ◽

Bruno Pires ◽

...

Keyword(s):

Electron Donor ◽

Functional Group ◽

Photoexcited Electron ◽

One Pot ◽

Quaternary Centers ◽

Metal Free ◽

Acceptor Complex ◽

Catalyst Free ◽

Donor Acceptor ◽

Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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ChemInform Abstract: Scope and Mechanistic Analysis of the Enantioselective Synthesis of Allenes by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement Between Donor/Acceptor Carbenoids and Propargylic Alcohols.

ChemInform ◽

10.1002/chin.201309061 ◽

2013 ◽

Vol 44 (9) ◽

pp. no-no

Author(s):

Zhanjie Li ◽

Vyacheslav Boyarskikh ◽

Joern H. Hansen ◽

Jochen Autschbach ◽

Djamaladdin G. Musaev ◽

...

Keyword(s):

Sigmatropic Rearrangement ◽

Enantioselective Synthesis ◽

Propargylic Alcohols ◽

Mechanistic Analysis ◽

Donor Acceptor

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Metal-Free C-Se Cross-Coupling Enabled by Photoinduced Intermolecular Charge Transfer

Chemical Communications ◽

10.1039/d1cc06152f ◽

2021 ◽

Author(s):

Chen Zhu ◽

Serik Zhumagazy ◽

Huifeng Yue ◽

Magnus Rueping

Keyword(s):

Charge Transfer ◽

Visible Light ◽

Electron Donor ◽

Cross Coupling ◽

Metal Free ◽

Intermolecular Charge Transfer ◽

Donor Acceptor

Metal-free C-Se cross-couplings via the formation of electron-donor-acceptor (EDA) complexes have been developed. The visible-light induced reactions can be applied for the synthesis of a series of unsymmetrical diaryl selenides...

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Synthesis and characterization of a novel unsymmetrical metal-free phthalocyanine with donor-acceptor substituents

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.5570310453 ◽

1994 ◽

Vol 31 (4) ◽

pp. 1017-1020 ◽

Cited By ~ 24

Author(s):

Yunqi Liu ◽

Daoben Zhu ◽

Tatsuo Wada ◽

Akira Yamada ◽

Hiroyuki Sasabe

Keyword(s):

Synthesis And Characterization ◽

Metal Free ◽

Donor Acceptor

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Metal-Free Catalysis: A Redox-Active Donor–Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2 Reduction to CH4

Journal of the American Chemical Society ◽

10.1021/jacs.1c07916 ◽

2021 ◽

Author(s):

Soumitra Barman ◽

Ashish Singh ◽

Faruk Ahamed Rahimi ◽

Tapas Kumar Maji

Keyword(s):

Visible Light ◽

Co2 Reduction ◽

Metal Free ◽

Conjugated Microporous Polymer ◽

Redox Active ◽

Microporous Polymer ◽

Visible Light Driven ◽

Donor Acceptor ◽

Active Donor

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A Formal Metal-Free γ-Arylation of 1,3-Dicarbonyl Compounds via a Sequence of Isomerization/1,4-Addition/[3,3]-Sigmatropic Rearrangement

Green Chemistry ◽

10.1039/d1gc02856a ◽

2021 ◽

Author(s):

Shi-Chao Lu ◽

Fuqiang Wen ◽

Xidong Guan

Keyword(s):

Sigmatropic Rearrangement ◽

Mechanistic Studies ◽

Dicarbonyl Compounds ◽

Metal Free

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide an unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a...

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