Abstract

Benzosiloles and their π-extended derivatives are present in many important advanced materials due to their excellent physical properties. Especially, they have found many potential applications in the development of novel electronic materials such as OLEDs, semiconductors and solar cells. In this review, we have summarized several main approaches to construct (di)benzosilole derivatives and (benzo)siloles fused to aromatic five- and six-membered heterocycles.

Highlights

  • Benzosiloles and their π-extended derivatives have attracted much attention because of their extraordinary properties in comparison with other well-known organic materials [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17]

  • In 1955, the first synthesis of 9,9-diphenylsilafluorene was reported by Gilman and Gorsich [25]

  • The first oxidative addition (OA) of Pd catalyst to starting material occurred to afford arylpalladium which could undergo intramolecular electrophilic substitution (ES) to give the palladacycle intermediate, followed by a 1,2-migration step leading to cationic palladacycle

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Summary

Introduction

Benzosiloles and their π-extended derivatives have attracted much attention because of their extraordinary properties in comparison with other well-known organic materials [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17]. Conventional methods for the synthesis of dibenzosilole derivatives are often based on the metal-halide exchange of dihalobiarenes, followed by cyclization with dichlorosilanes [21,22,23,24]. These reactions are often carried out under very low temperature conditions and/or for a long reaction time.

Conventional Metal-Halide Exchange Method
Metal-Catalyzed C–H Activations
Transition Metal-Catalyzed C–H Silylations
Synthesis of Dibenzosilole Derivatives via a sila-Friedel-Crafts Reaction
Cyclizations via Silyl Radicals
Findings
Conclusions
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