Single operation palladium catalysed C(sp3)-H functionalisation of tertiary aldehydes: investigations into transient imine directing groups.

Single operation palladium catalysed C(sp3)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups† †Electronic supplementary information (ESI) available: Experimental procedures and characterisation data; full optimisation table for arylation of pivaldehyde; studies on imine formation/hydrolysis in AcOD-d 4; reaction plots with time for different directing groups and catalyst loading and addition of DMSO; effect of TFA addition; 1H NMR spectra of sample aldehyde regions; 1H and 13C NMR spectra for characterised compounds and crystal structure data. CCDC 1534094. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01218g Click here for additional data file. Click here for additional data file.

Silver-Free Palladium-Catalyzed C(sp3)-H Arylation of Saturated Bicyclic Amine Scaffolds.

Herein, we report a silver-free Pd(II)-catalyzed C(sp3)-H arylation of saturated bicyclic and tricyclic amine scaffolds. The reaction provides good yields using a range of aryl iodides and aryl bromides including functionalized examples bearing aldehydes, ketones, esters, free phenols, and heterocycles. The methodology has been applied to medicinally relevant scaffolds. Two of the intermediate ...

Palladium-catalysed direct arylation of thiophenes tolerant to silyl groups.

The palladium catalysed 5-arylation of 2-(trimethylsilyl)thiophene with aryl bromides via C-H bond functionalisation allows the synthesis of arylated silylthiophenes in only one step.

Challenges and opportunities for alkane functionalisation using molecular catalysts

The conversion of vast low-value saturated hydrocarbons into valuable chemicals is of great interest. Thanks to the progression of organometallic and coordination chemistry, transition metal catalysed C sp3-H bond functionalisation has now become a powerful tool for alkane transformations. Specifically, methods for alkane functionalisation include radical initiated C-H functionalisation, carben...

The total synthesis of K-252c (staurosporinone) via a sequential C-H functionalisation strategy.

A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) via a sequential C-H functionalisation strategy is reported. The route exploits direct functionalisation reactions around a simple arene core and comprises of two highly-selective copper-catalysed C-H arylations, a copper-catalysed C-H amination and a palladium-catalysed C-H carbonylation, which build up the structur...