Rhodium-Catalyzed 2-Arylphenol-Derived Six-Membered Silacyclization: Straightforward Access toward Dibenzooxasilines and Silicon-Containing Planar Chiral Metallocenes | doi.page

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Rhodium-Catalyzed 2-Arylphenol-Derived Six-Membered Silacyclization: Straightforward Access toward Dibenzooxasilines and Silicon-Containing Planar Chiral Metallocenes

ACS Catalysis2018Vol. 8(9), pp. 7997–8005

Citations Over TimeTop 10% of 2018 papers

Wentao Zhao, Zhuoqun Lu, Hanliang Zheng, Xiao‐Song Xue, Dongbing Zhao

Abstract

The C/Si switch strategy has been regarded as a useful and efficient strategy for the discovery of drugs and materials. Thus, development of a methodology to access diverse silacycles is of great significance and in great demand. Among these, C–H bond silylation provides a powerful and straightforward synthetic method to form diverse silacycles in an atom- and step-economical fashion. However, C–H bond silylation has not been used to access any six-membered silicon-bridged π-conjugated scaffolds and enantioselective six-membered C–H silylation has never been presented. Herein, we successfully accessed diverse six-membered π-conjugated dibenzooxasilines via C–H bond silylation and investigated their photophysical properties. Furthermore, we realized enantioselective six-membered C–H siylation to directly afford planar chiral metallocene oxasilolanes with high ee (up to 95% ee). We also demonstrated the synthetic usefulness of dibenzooxasilines and planar chiral metallocene-fused benzooxasilolines as valuable synthetic intermediates via diverse additional transformations. Moreover, six-membered silicon-bridged ladder π-conjugated systems were designed and rapidly constructed by using our methods. The “isomerization” and “silicon” effects on molecular geometries and photophysical properties were also evaluated in detail.

Citations Over TimeTop 10% of 2018 papers

Abstract

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