Phenyl iodonium triflate benzyne precursor

Phenyl[2-(trimethylsilyl)phenyl]iodonium triflate (226) has emerged as a superior benzyne precursor i.e., admixture of 226 with tetra-n-butylammonium fluoride (TBAF) enables the generation of benzyne in dichloromethane at room temperature (95JCS(CC)983). When organo azides or -nitrones are available in the reaction medium, high yields of the benzotriazoles 227 or benzisoxazolines 228 are obtained (Scheme 62) (98HC205). 

Benzyne is one of a group of reactive intermediates widely applicable to organic synthesis.2"5 The title hypervalent iodine-benzyne precursor, (phenyl)[2-(trimethylsilyl)phenyl]iodonium triflate 2,6 is prepared by only two steps from commercially available reagents. Products 1 and 2 are stable and easily purified. The hypervalent iodine-benzyne precursor 2 is obtained as a stable solid and handled without any precautions. More importantly, benzyne is generated by using... 

PHENYL)[2-(TRIMETHYLSILYL)PHENYL]IODONIUM TRIFLATE. AN EFFICIENT AND MILD BENZYNE PRECURSOR. 

Phenyl)[2-(Trimethylsilyl)phenyl]iodonium Triflate. An Efficient and Mild Benzyne Precursor. 

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