Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties.

ABSTRACT: Herein a regioselective addition/annulation strategy of ferrocenyl (Fc) thioamides with alkynes to construct thienylferrocene (ThienylFc) structures, involving a rhodium-catalyzed C-H activation, an unusual C2-selective addition of 1,3-diyne, and an unexpected intramolecular sulfur-transfer rearrangement process is described. In this protocol, thioamide not only serves as a directing group to activate the ortho-C-H bond of the ferrocene, but also as a sulfur source to form the thiophene ring. The resulting carboxylic ester group after sulfur transfer can act as a linkage to construct extended π-conjugated ferrocenes (OCTFc) with luminescent properties. ThienylFc displays effective fluorescence quenching due to the photoinduced electron transfer (PET) from the Fc unit to the excited

SUBMITTER: Yan L 

PROVIDER: S-EPMC8162306 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature