Visible light mediated, metal-free carbene transfer reactions of diazoalkanes with propargylic alcohols

2019 ◽  
Vol 55 (33) ◽  
pp. 4881-4884 ◽  
Author(s):  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Transfer Reactions ◽  
High Yield ◽  
Propargylic Alcohols ◽  
Metal Free ◽  
Sterically Demanding ◽  
Donor Acceptor ◽  
Carbene Transfer

The photolysis of donor–acceptor diazoalkanes in the presence of propargylic alcohols furnishes valuable, sterically demanding tetra-substituted cyclopropenes in high yield under metal-free conditions.

Sustainable Carbene Transfer Reactions with Iron and Light

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1929-1934 ◽  
Author(s):  
Claire Empel ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Transfer Reaction ◽  
Reactive Intermediates ◽  
Building Blocks ◽  
Transfer Reactions ◽  
Iron Catalysts ◽  
Metal Free ◽  
Scalable Applications ◽  
Carbene Transfer

Carbenes are versatile, highly reactive intermediates with great importance in chemistry. We recently reported on our findings on safe and scalable applications of hazardous diazoacetonitrile using cheap and commercially available iron catalysts in efficient carbene transfer reactions, ranging from cyclopropanation towards C–H functionalization reactions for the synthesis of biologically important building blocks. More lately, we uncovered the reactivity of diazoalkanes under photochemical conditions using visible light and were able to demonstrate a variety of different, metal-free carbene transfer reactions, which now open up new sustainable ways for the construction of small functional molecules.1 Introduction2 Iron-Catalyzed Carbene Transfer Reactions of Diazoacetonitrile3 Metal-free Carbene Transfer Reaction with Visible Light4 Summary

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

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...

Visible-light driven, metal-free hydroalkylation of alkenes mediated by electron donor-acceptor complex using benzothiazolines

2021 ◽  
Author(s):  
Tatsuhiro Uchikura ◽  
Tatsuya Fujii ◽  
Kaworuko Moriyama ◽  
Takahiko Akiyama
Keyword(s):  
Visible Light ◽  
Electron Donor ◽  
Metal Free ◽  
Acceptor Complex ◽  
Visible Light Driven ◽  
Donor Acceptor

A Metal‐Free Donor–Acceptor Covalent Organic Framework Photocatalyst for Visible‐Light‐Driven Reduction of CO 2 with H 2 O

ChemSusChem ◽  
2020 ◽  
Vol 13 (7) ◽  
pp. 1725-1729 ◽  
Author(s):  
Kai Lei ◽  
Di Wang ◽  
Liqun Ye ◽  
Mingpu Kou ◽  
Yu Deng ◽  
...  
Keyword(s):  
Visible Light ◽  
Metal Free ◽  
Covalent Organic Framework ◽  
Visible Light Driven ◽  
Donor Acceptor ◽  
Organic Framework

scholarly journals Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions

2019 ◽  
Vol 10 (34) ◽  
pp. 7958-7963 ◽  
Author(s):  
Ban Wang ◽  
Isaac G. Howard ◽  
Jackson W. Pope ◽  
Eric D. Conte ◽  
Yongming Deng
Keyword(s):  
Iron Complexes ◽  
Iron Complex ◽  
Diazo Compounds ◽  
Transfer Reactions ◽  
Donor Acceptor ◽  
Carbene Transfer ◽  
First Time

The bis(imino)pyridine iron complex, for the first time, is developed as an effective metal carbene catalyst for carbene transfer reactions of donor–acceptor diazo compounds.

Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C−C Bond Formations under Visible Light

2018 ◽  
Vol 360 (22) ◽  
pp. 4312-4318 ◽  
Author(s):  
Lei Wang ◽  
Jeehye Byun ◽  
Run Li ◽  
Wei Huang ◽  
Kai A. I. Zhang
Keyword(s):  
Visible Light ◽  
Molecular Design ◽  
Metal Free ◽  
Donor Acceptor

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

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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