1582787-70-9Relevant articles and documents
Synthesis of fluorinated aromatic compounds by one-pot benzyne generation and nucleophilic fluorination
Ikawa, Takashi,Masuda, Shigeaki,Nishiyama, Tsuyoshi,Takagi, Akira,Akai, Shuji
, p. 475 - 480 (2014/04/03)
The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential reactions in one-pot: the nonaflylation of phenols, benzyne generation, and nucleophilic fluorination of the benzynes. The regioselectivities of these reactions are controlled by the substituents at the C3-position of the benzynes. CSIRO 2014.