Efficient and facile Ar-Si bond cleavage by montmorillonite KSF: synthetic and mechanistic aspects of solvent-free protodesilylation studied by solution and solid-state MAS NMR.
A facile and efficient method for the cleavage of the Ar-Si bond of various aryl trimethyl silanes is described. When adsorbed on montmorillonite KSF (mont KSF), these arylsilanes readily undergo a solvent-free protodesilylation to the corresponding arenes at room temperature in excellent yields. This approach seems to be superior to the traditional mild methods (i.e., desilylation by TFA, TBAF, CsF), in terms of reaction yield, rate, and environmentally benign conditions. Some mechanistic studies using both solution and solid-state magic-angle spinning (SS MAS) (1)H NMR are also presented.
Department of Organic Chemistry, Israel Institute for Biological Research, Ness-Ziona 74100, Israel. yossiz@iibr.gov.il
Yossi
Y
Zafrani
Eytan
E
Gershonov
Ishay
I
Columbus
D001128:Argon / Q000737:chemistry*; D001546:Bentonite / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011522:Protons; D012821:Silanes / Q000737:chemistry; D012828:Silicones / Q000737:chemistry*; D012996:Solutions; D012997:Solvents
D011522:Protons; D012821:Silanes; D012828:Silicones; D012996:Solutions; D012997:Solvents; C523398:montmorillonite KSF; D001546:Bentonite; D001128:Argon