Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane

Abstract

Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl)silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis(benzosilole) compound, shows electron drift mobility as high as 6 x 10-4 cm2/Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.

Synthetic Strategy for Multisubstituted Fused Furan Compounds Using Main-Group Metal Reagents

“…This concept can also be applied to the synthesis of other heterocyclic compounds such as indoles, 43 phospholes, 44 or siloles, 45 as well as π-conjugated hydrocarbon compounds. 5i,j,46,47 Some of the new fused furan compounds were found to be viable organic semiconductor materials that are aerobically, thermally, and electrochemically stable.…”

Rhodium-Catalyzed Coupling of 2-Silylphenylboronic Acids with Alkynes Leading to Benzosiloles: Catalytic Cleavage of the Carbon−Silicon Bond in Trialkylsilyl Groups

“…Diarylalkynes also served as good coupling partners in the present catalysis, furnishing densely arylated benzosilole derivatives 11-13, which constitute an important class of compounds in the context of organic electronic materials. 11 Unsymmetrical alkynes proved to be applicable as well. Arylalkylacetylenes underwent a twocomponent annulation to form benzosiloles 14 and 15, which bear an aryl group at the 2-position in the major isomer.…”

Syntheses, Optical Properties, and Theoretical Investigation of Silafluorenes and Spirobisilafluorenes Bearing Electron‐Donating Aminostyryl Arms around a Silafluorene Core

“…[5] Its high abundance in the earths crust is also advantageous from the point of view of applications. [6] Especially, silole [1b, 5, 7] and its benzo-fused derivatives (benzosilole [8] and dibenzosilole (silafluorene) [9] ), are the most important silicon-containing p-conjugated systems, because of their improved optoelectronic properties. The Si À C bonds of the silole derivatives are fixed perpendicular to p orbitals on the ring, and thus s*A C H T U N G T R E N N U N G (SiÀC)-p* hyperconjugation is effective.…”