1582806-75-4

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 1582806-46-9 (S)-2-phthalimido-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 
• 4192-28-3 Phth-L-Ala-OH 
• 4306-25-6 (S)-2-phthalimidopropionyl chloride 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 18954-74-0 (4-bromophenyl)triethoxysilane 

Relevant academic research and scientific papers

Functionalized Polymer-Supported Pyridine Ligands for Palladium-Catalyzed C(sp3)-H Arylation

The use of ligands to tune the reactivity and selectivity of transition-metal catalysts for C(sp3)-H bond activation is a current central challenge. One of us previously developed an uncommon example of a homogeneous catalyst that performs controlled C(sp3)-H arylation using pyridine derivatives as ligands, along with Pd [Science, 2014, 343, 1216-1220]. In this work, we report a functionalizable and tunable polymer support used in the immobilization of pyridine derivatives that yields a soluble, polymeric ligand platform facilitating C(sp3)-H activation reactions with good yields, selectivities differing from the homogeneous catalyst, and recovery of Pd. Unlike the homogeneous system, the supported catalysts in Pd-catalyzed C-H monoarylation reactions respond sensitively to the steric hindrance of the coupling partners.

Ligand-Enabled Cross-Coupling of C(sp3)-H Bonds with Arylsilanes

Pd(II)-catalyzed cross-coupling of C(sp3)-H bonds with organosilicon coupling partners has been achieved for the first time. The use of a newly developed quinoline-based ligand is essential for the cross-coupling reactions to proceed.

LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS

The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.

Ligand-controlled C(sp3)-H arylation and olefination in synthesis of unnatural chiral α-amino acids

The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: The former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-β-Ar?-α-amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.