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Synfacts 2025; 21(07): 695
DOI: 10.1055/a-2601-4025
Metals in Synthesis

Regioselective Synthesis of Eight-Membered Benzosilacycles via Ring Expansion of Silacyclobutanes

Contributor(s):
Mark Lautens 
,
Mrinmay Baidya
Guo Z, Ye J, Zhang Y, Wang D, Yu X, Li C, Wu Y *, Liu Z *. Zhengzhou University, P. R. China
Modular and Regioselective Synthesis of Eight-Membered Benzosilacycles Enabled by Ring Expansion of Silacyclobutanes with Aryl Halides and Alkynes.

ACS Catal. 2025;
15: 7066-7078
DOI: 10.1021/acscatal.5c01177
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Keywords

palladium catalysis - ring expansion - benzosilacycles - multicomponent reaction

Significance

This work enables the efficient synthesis of eight-membered benzosilacycles via palladium-catalyzed alkyne insertion/C–H activation/ring expansion. This modular method was exemplified with over 80 examples, showing high selectivity and scalability, while mechanistic studies explained the regiocontrol.


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Comment

The authors present a palladium-catalyzed ring-expansion method for synthesizing eight-membered benzosilacycles with excellent regioselectivity. Supported by DFT studies, this approach offers broad functional group (FG) tolerance, a gram-scale synthesis, and versatile derivatization.


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Publication History

Article published online:
23 June 2025

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