A Transition??Metal??Free Synthesis of Fluorinated Naphthols

JM Hammann, TA Unzner…

Index: Hammann, Jeffrey M.; Unzner, Teresa A.; Magauer, Thomas Chemistry - A European Journal, 2014 , vol. 20, # 22 p. 6733 - 6738

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Citation Number: 9

Abstract

Abstract Herein, we describe a transition-metal-free protocol for the conversion of simple 2- allyl-3-(trifluoromethyl) phenols into substituted 5-fluoronaphthalen-1-ols. The key events of this reaction include the selective activation of two C [BOND] F bonds and formation of an intermediate hexatriene system, which undergoes a 6π electrocyclization, followed by rearomatization. This concept enables the rapid conversion (three steps) of various ...