2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors

Autor: Takashi Ikawa, Shuji Akai, Hiroki Nakajima, Shigeaki Masuda
Rok vydání: 2017
Předmět:
Zdroj: The Journal of organic chemistry. 82(8)
ISSN: 1520-6904
Popis: 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.
Databáze: OpenAIRE