Visible-Light-Induced Acylsilylation of Nitrosoarenes for Synthesis of N-Arylhydroxamic Acid Silicon Esters
Yin-Xia Wang1, Chuang Wang1, Na Li1
1College of Energy and Chemical Engineering, Luoyang Institute of Science and Technology, Luoyang 471023, P. R. China.
Abstract:
A visible-light-induced acylsilylation of nitrosoarenes with acylsilanes has been developed under transition-metal-free conditions. This reaction proceeds via a photoinduced [1,2]-Brook rearrangement of acylsilanes to generate nucleophilic siloxycarbenes, which add to the electrophilic nitrogen atom of nitrosoarenes, affording a range of N-arylhydroxamic acid silicon esters. Control experiments support a singlet carbene pathway. This method is operationally simple, proceeds under mild conditions, and exhibits a broad substrate scope, offering an atom-economical and practical approach to an important class of hydroxamic acid derivatives.
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