Visible-Light-Promoted CC Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals

2012 ◽  
Vol 124 (32) ◽  
pp. 8174-8177 ◽  
Author(s):  
Shunyou Cai ◽  
Xinyang Zhao ◽  
Xinbo Wang ◽  
Qisong Liu ◽  
Zigang Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Iminium Ions

Visible-Light-Promoted CC Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals

2012 ◽  
Vol 51 (32) ◽  
pp. 8050-8053 ◽  
Author(s):  
Shunyou Cai ◽  
Xinyang Zhao ◽  
Xinbo Wang ◽  
Qisong Liu ◽  
Zigang Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Iminium Ions

ChemInform Abstract: Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals.

ChemInform ◽  
2013 ◽  
Vol 44 (3) ◽  
pp. no-no
Author(s):  
Shunyou Cai ◽  
Xinyang Zhao ◽  
Xinbo Wang ◽  
Qisong Liu ◽  
Zigang Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Iminium Ions

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

ChemInform Abstract: Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C-C-Bond Cleavage Reactions.

ChemInform ◽  
2013 ◽  
Vol 44 (29) ◽  
pp. no-no
Author(s):  
Shaoqun Zhu ◽  
Arindam Das ◽  
Lan Bui ◽  
Hanjun Zhou ◽  
Dennis P. Curran ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Photoredox Catalysis ◽  
Cleavage Reactions

scholarly journals Light-Driven Depolymerization of Native Lignin Enabled by Proton- Coupled Electron Transfer

2019 ◽  
Author(s):  
Suong Nguyen ◽  
Phillip Murray ◽  
Robert Knowles
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Bond Cleavage ◽  
Direct Conversion ◽  
Alkoxy Radical ◽  
Radical Intermediate ◽  
Polymer Backbone ◽  
Good Efficiency ◽  
Chemical Reagents ◽  
Proton Coupled Electron Transfer

<div><p>Here we report a catalytic, light-driven method for the redox-neutral depolymerization of native lignin biomass at ambient temperature. This transformation proceeds via a proton-coupled electron-transfer (PCET) activation of an alcohol O–H bond to generate a key alkoxy radical intermediate, which then drives the <i>β</i>-scission of a vicinal C–C bond. Notably, this depolymerization is driven solely by visible light irradiation, requiring no stoichiometric chemical reagents and producing no stoichiometric waste. This method exhibits good efficiency and excellent selectivity for the activation and fragmentation of <i>β</i>-O-4 linkages in the polymer backbone, even in the presence of numerous other PCET-active functional groups. DFT analysis suggests that the key C–C bond cleavage reactions produce non-equilibrium product distributions, driven by excited-state redox events. These results provide further evidence that visible-light photocatalysis can serve as a viable method for the direct conversion of lignin biomass into valuable arene feedstocks.</p></div>

scholarly journals One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

2014 ◽  
Vol 10 ◽  
pp. 2981-2988 ◽  
Author(s):  
Joshua P Barham ◽  
Matthew P John ◽  
John A Murphy
Keyword(s):  
Visible Light ◽  
Tertiary Amines ◽  
One Pot ◽  
Carbon Nucleophiles ◽  
Iminium Salts ◽  
Iminium Ions ◽  
Nucleophilic Trapping ◽  
Limited Scope

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp2–C(CO) bond cleavage

2020 ◽  
Vol 18 (38) ◽  
pp. 7549-7553
Author(s):  
Rui Ma ◽  
Jie Feng ◽  
Kuili Zhang ◽  
Beichen Zhang ◽  
Ding Du
Keyword(s):  
Visible Light ◽  
Bond Cleavage

An olefinic difunctionalization method of enones was presented here via aerobic visible-light catalysis.

Visible-Light-Driven Selective Alkenyl C–P Bond Cleavage of Allenylphosphine Oxides

2019 ◽  
Vol 21 (7) ◽  
pp. 1994-1998 ◽  
Author(s):  
Kai Wei ◽  
Kai Luo ◽  
Fang Liu ◽  
Lei Wu ◽  
Li-Zhu Wu
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Visible Light Driven
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