Palladium-Catalyzed Tandem Reaction of Yne-Propargylic Carbonates with Boronic Acids: A Simple Method for the Synthesis of Fused Aromatic Rings through Allene-Mediated Electrocyclization

2004 ◽  
Vol 10 (21) ◽  
pp. 5338-5344 ◽  
Author(s):  
Feng Wang ◽  
Xiaofeng Tong ◽  
Jiang Cheng ◽  
Zhaoguo Zhang
Keyword(s):  
Boronic Acids ◽  
Tandem Reaction ◽  
Aromatic Rings ◽  
Simple Method ◽  
Palladium Catalyzed

scholarly journals Pd(II)-catalyzed enantioselective C(sp3)–H arylation of cy-clopropanes and cyclobutanes guided by tertiary alkyla-mines.

2021 ◽  
Author(s):  
Matthew Gaunt ◽  
Jesus Rodrigalvarez ◽  
Luke Reeve ◽  
Javier Miro
Keyword(s):  
Small Molecules ◽  
Computational Analysis ◽  
Structural Features ◽  
Biological Properties ◽  
Boronic Acids ◽  
Biologically Active ◽  
Simple Method ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Palladium Catalyzed

ABSTRACT: Strained aminomethyl-cycloalkanes are a recurrent scaffold in medicinal chemistry due to their unique structural features that give rise to a range of biological properties. Here, we report a palladium-catalyzed enantioselective C(sp3)–H arylation of aminome-thyl-cyclopropanes and -cyclobutanes with aryl boronic acids. A range of native tertiary alkylamine groups are able to direct C–H cleavage and forge carbon-aryl bonds on the strained cycloalkanes framework as single diastereomers and with excellent enantiomeric ratios. Cen-tral to the success of this strategy is the use of a simple N-acetyl amino acid ligand, which not only controls the enantioselectivity but also promotes -C–H activation of over other pathways. Computational analysis of the cyclopalladation step provides an understanding of how enantioselective C–H cleavage occurs and revealed distinct transition structures to our previous work on enantioselective desymme-trization of N-iso-butyl tertiary alkylamines. This straightforward and operationally simple method simplifies the construction of func-tionalized aminomethyl-strained cycloalkanes, which we believe will find widespread use in academic and industrial settings relating to the synthesis of biologically active small molecules.

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>

Palladium-Catalyzed Selective CH Activation: A Simple Method to Synthesize C-3 Site Arylated Quinoline Derivatives

2016 ◽  
Vol 358 (3) ◽  
pp. 375-379 ◽  
Author(s):  
Yongqin He ◽  
Zhaoyang Wu ◽  
Chaowei Ma ◽  
Xiaoqiang Zhou ◽  
Xingxing Liu ◽  
...  
Keyword(s):  
Quinoline Derivatives ◽  
Simple Method ◽  
Palladium Catalyzed

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

Synthesis ◽  
2021 ◽  
Author(s):  
Antonella Goggiamani ◽  
Antonia Iazzetti ◽  
Antonio Arcadi ◽  
Andrea Calcaterra ◽  
Marco Chiarini ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Experimental Procedure ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Reaction Works

AbstractThe palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Highly Regioselective Synthesis of Spirocyclic Compounds by a Palladium-Catalyzed Intermolecular Tandem Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (52) ◽  
Author(s):  
Hai-Peng Bi ◽  
Xue-Yuan Liu ◽  
Fa-Rong Gou ◽  
Li-Na Guo ◽  
Xin-Hua Duan ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Tandem Reaction ◽  
Palladium Catalyzed ◽  
Spirocyclic Compounds

Access to chiral tetrahydrofluorenes through a palladium-catalyzed enantioselective tandem intramolecular Heck/Tsuji–Trost reaction

2019 ◽  
Vol 55 (26) ◽  
pp. 3769-3772 ◽  
Author(s):  
Ying Zhang ◽  
Hong-Cheng Shen ◽  
Yang-Yang Li ◽  
Yong-Shuang Huang ◽  
Zhi-Yong Han ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed

A palladium-catalyzed enantioselective tandem reaction of 2,5-cyclohexadienyl-substituted aryl iodides and carbon or heteroatom nucleophiles has been successfully established by using a chiral H8-BINOL-based phosphoramidite ligand.

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