scholarly journals Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

2016 ◽  
Vol 55 (23) ◽  
pp. 6776-6779 ◽  
Author(s):  
Eleonora Fava ◽  
Anthony Millet ◽  
Masaki Nakajima ◽  
Sebastian Loescher ◽  
Magnus Rueping
Keyword(s):  
Visible Light ◽  
Amino Alcohols ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Carbonyl Derivatives ◽  
Vicinal Diamines

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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

Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis

2013 ◽  
Vol 15 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Yusuke Yasu ◽  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Visible Light Driven

Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis

RSC Advances ◽  
2015 ◽  
Vol 5 (56) ◽  
pp. 44928-44932 ◽  
Author(s):  
Milan Dinda ◽  
Chandan Bose ◽  
Tridev Ghosh ◽  
Soumitra Maity
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Dehydrogenative Coupling

A visible light mediated cross-dehydrogenative-coupling (CDC) reaction has been developed for the synthesis of N-hydroxyester derivatives from aldehydes and N-hydroxyimides.

Visible-Light-Induced Photoredox Catalysis with a Tetracerium-Containing Silicotungstate

2014 ◽  
Vol 53 (21) ◽  
pp. 5356-5360 ◽  
Author(s):  
Kosuke Suzuki ◽  
Fei Tang ◽  
Yuji Kikukawa ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis

ChemInform Abstract: Visible Light Photooxidative Cyclization of Amino Alcohols to 1,3-Oxazines.

ChemInform ◽  
2013 ◽  
Vol 44 (30) ◽  
pp. no-no
Author(s):  
Cheryl L. Mathis ◽  
Brandi M. Gist ◽  
Conerd K. Frederickson ◽  
Katie M. Midkiff ◽  
Christopher C. Marvin
Keyword(s):  
Visible Light ◽  
Amino Alcohols
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