Nucleophilic Addition of Boronic Acids to Imines (The Petasis Reaction)

2008 ◽  
pp. 1
Author(s):  
M. J. Bingham ◽  
M. F. Greaney
Keyword(s):  
Nucleophilic Addition ◽  
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.

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 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

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

Neoglycopeptide Synthesis by Suzuki-Miyaura Couplings between Glycosyl Aryl Boronic Acids and Iodopeptides

2014 ◽  
Vol 21 (10) ◽  
pp. 1004-1010
Author(s):  
Guohua Chen ◽  
Xiangying Gu ◽  
Lin Chen ◽  
Xin Wang ◽  
Yue-Lei Chen ◽  
...  
Keyword(s):  
Boronic Acids

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

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