scholarly journals Photoredox-Catalyzed Multicomponent Petasis Reaction in Batch and Continuous Flow with Alkyl Boronic Acids

iScience ◽  
2021 ◽  
pp. 103134
Author(s):  
Monica Oliva ◽  
Prabhat Ranjan ◽  
Serena Pillitteri ◽  
Guglielmo Attilio Coppola ◽  
Monica Messina ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Boronic Acids ◽  
Petasis Reaction

Petasis Reaction of Activated Quinoline and Isoquinoline with Various Boronic Acids.

ChemInform ◽  
2005 ◽  
Vol 36 (34) ◽  
Author(s):  
Yu Mi Chang ◽  
Seung Hwan Lee ◽  
Mi Hye Nam ◽  
Min Young Cho ◽  
Young Sang Park ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Petasis Reaction

Anomalies in the Stereoselectivity of the Petasis Reaction Using Styrenyl Boronic Acids

2011 ◽  
Vol 64 (1) ◽  
pp. 62 ◽  
Author(s):  
Quentin I. Churches ◽  
James K. Johnson ◽  
Nathan L. Fifer ◽  
Craig A. Hutton
Keyword(s):  
Glyoxylic Acid ◽  
Coupling Reaction ◽  
Boronic Acids ◽  
High Yield ◽  
Amino Acid Derivatives ◽  
Efficient Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Petasis Reaction ◽  
Efficient Route ◽  
Unsaturated Amino Acid

The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives.

scholarly journals Unlocking the Accessibility of Alkyl Radicals from Boronic Acids through Hydrogen-bond Assisted Organophotoredox Activation

2021 ◽  
Author(s):  
Prabhat Ranjan ◽  
Serena Pillitteri ◽  
Guglielmo Coppola ◽  
Monica Oliva ◽  
Erik V. Van der Eycken ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Unnatural Amino Acids ◽  
Alkyl Radical ◽  
Boronic Acids ◽  
Oxidation Potential ◽  
Radical Species ◽  
Alkyl Radicals ◽  
Hydrogen Bonding Interactions ◽  
High Oxidation ◽  
Selective Generation

Despite their prevalence in organic synthesis, the application of boronic acids (BAs) as alkyl radical precursors in visible-light assisted photocatalyzed reactions has been limited by their high oxidation potential. This study demonstrates the remarkable ability of amide solvents viz. DMA (N,N-dimethylacetamide) to participate in hydrogen-bonding interactions with BAs, thus enabling the modulation of their oxidation potential towards the generation of alkyl radicals. The developed protocol is simple, robust and demonstrates broad applicability for alkylation, allylation and elimination reactions in batch and continuous flow. The application towards dehydroalanine allows the synthesis of unnatural amino acids. Furthermore, the chemo-selective generation of radical species from BAs, in the presence of boronic ester-containing molecules, is now feasible, endorsing plausible boron-selective (bio-) orthogonal modifications.

A Metal-free Petasis reaction towards the synthesis of N-(-substituted)alkyl sulfoximines/sulfonimidamides

2021 ◽  
Author(s):  
K. Natarajan ◽  
Irfana Jesin C. P. ◽  
A.Antony Haritha Mercy ◽  
Ganesh Chandra Nandi
Keyword(s):  
Boronic Acids ◽  
One Pot ◽  
Metal Free ◽  
Petasis Reaction ◽  
Novel Approach

Herein, we disclose a metal-free novel approach for the synthesis of N-( -substituted)alkyl sulfoximines/sulfonimidamides via one-pot multicomponent Petasis reactions of aryl boronic acids, ortho-hydroxyarylaldehydes and sulfoximines/sulfonimidamides in moderate to very...

Petasis reaction of activated quinoline and isoquinoline with various boronic acids

2005 ◽  
Vol 46 (17) ◽  
pp. 3053-3056 ◽  
Author(s):  
Yu Mi Chang ◽  
Seung Hwan Lee ◽  
Mi Hye Nam ◽  
Min Young Cho ◽  
Young Sang Park ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Petasis Reaction

scholarly journals Unlocking the Accessibility of Alkyl Radicals from Boronic Acids through Hydrogen-bond Assisted Organophotoredox Activation

2021 ◽  
Author(s):  
Prabhat Ranjan ◽  
Serena Pillitteri ◽  
Guglielmo Coppola ◽  
Monica Oliva ◽  
Erik V. Van der Eycken ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Unnatural Amino Acids ◽  
Alkyl Radical ◽  
Boronic Acids ◽  
Oxidation Potential ◽  
Radical Species ◽  
Alkyl Radicals ◽  
Hydrogen Bonding Interactions ◽  
High Oxidation ◽  
Selective Generation

Despite their prevalence in organic synthesis, the application of boronic acids (BAs) as alkyl radical precursors in visible-light assisted photocatalyzed reactions has been limited by their high oxidation potential. This study demonstrates the remarkable ability of amide solvents viz. DMA (N,N-dimethylacetamide) to participate in hydrogen-bonding interactions with BAs, thus enabling the modulation of their oxidation potential towards the generation of alkyl radicals. The developed protocol is simple, robust and demonstrates broad applicability for alkylation, allylation and elimination reactions in batch and continuous flow. The application towards dehydroalanine allows the synthesis of unnatural amino acids. Furthermore, the chemo-selective generation of radical species from BAs, in the presence of boronic ester-containing molecules, is now feasible, endorsing plausible boron-selective (bio-) orthogonal modifications.

Catalyst- and oxidant-free electrochemical para-selective hydroxylation of N-arylamides in batch and continuous-flow

2020 ◽  
Vol 22 (19) ◽  
pp. 6437-6443
Author(s):  
Cheng-Kou Liu ◽  
Meng-Yi Chen ◽  
Xin-Xin Lin ◽  
Zheng Fang ◽  
Kai Guo
Keyword(s):  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Continuous Flow ◽  
Quaternary Ammonium Salt ◽  
Selective Hydroxylation

A catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at rt in batch and continuous-flow was developed.

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