Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst

Ball, Liam T.; Lloyd-Jones, Guy C.; Russell, Christopher A.

doi:10.1021/ja408712e

All Outputs (24)

Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling (2019)
Journal Article

Thiophenols are versatile synthetic intermediates whose practical appeal is marred by their air sensitivity, toxicity and extreme malodor. Herein we report an efficient catalytic method for the preparation of S-aryl isothiouronium salts, and demonstr... Read More about Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling.

Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation (2016)
Journal Article
Corrie, T. J., Ball, L. T., Russell, C. A., & Lloyd-Jones, G. C. (2017). Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation. Journal of the American Chemical Society, 139(1), 245-254. https://doi.org/10.1021/jacs.6b10018

The intramolecular gold–catalyzed arylation of arenes by aryltrimethylsilanes has been investigated from both a mechanistic and preparative aspect. The reaction generates five to nine membered rings, and of the 44 examples studied, ten include a hete... Read More about Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation.

Self-control tames the coupling of reactive radicals (2014)
Journal Article
Lloyd-Jones, G. C., & Ball, L. T. (2014). Self-control tames the coupling of reactive radicals. Science, 345(6195), https://doi.org/10.1126/science.1256755

Highly reactive or unstable chemical reagents are challenging to prepare, store, and safely handle, so chemists frequently generate them in situ from convenient precursors. In an ideal case, the rate of release of the reagent would be matched to the... Read More about Self-control tames the coupling of reactive radicals.

Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst (2013)
Journal Article

The mechanism of gold-catalyzed coupling of arenes with aryltrimethylsilanes has been investigated, employing an improved precatalyst (thtAuBr3) to facilitate kinetic analysis. In combination with linear free-energy relationships, kinetic isotope eff... Read More about Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst.