Oligothiophene Synthesis by a General C-H Activation Mechanism: Electrophilic Concerted Metalation-Deprotonation (eCMD).

ABSTRACT: Oxidative C-H/C-H coupling is a promising synthetic route for the streamlined construction of conjugated organic materials for optoelectronic applications. Broader adoption of these methods is nevertheless hindered by the need for catalysts that excel in forging core semiconductor motifs, such as ubiquitous oligothiophenes, with high efficiency in the absence of metal reagents. We report a (thioether)Pd-catalyzed oxidative coupling method for the rapid assembly of both privileged oligothiophenes and challenging hindered cases, even at low catalyst loading under Ag- and Cu-free conditions. A combined experimental and computational mechanistic study was undertaken to understand how a simple thioether ligand, MeS(CH₂)₃SO₃Na, leads to such potent reactivity tow

SUBMITTER: Wang L 

PROVIDER: S-EPMC7377630 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature