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2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors
Takashi Ikawa1, Shigeaki Masuda1, Hiroki Nakajima1
1Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Abstract:
Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation, O-nonaflylation, and β-elimination under mild conditions using nonafluorobutanesulfonyl fluoride (NfF) and tetrabutylammonium triphenyldifluorosilicate (TBAT). The generated benzynes were trapped by various arynophiles to afford a wide variety of benzo-fused heterocycles.
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