David P Tilly, Subhendu S. Samanta, Anne‐Sophie Castanet
2006
Citations
0
Influential Citations
26
Citations
Journal
European Journal of Organic Chemistry
Abstract
Unprotected biphenyl-2-carboxylic acid can be cleanly metalated with sec-butyllithium at the position adjacent to the carboxylate and can then be subjected to site-selective electrophilic substitution. The remote C2′-position is attacked by the superbasic mixture of n-butyllithium and potassium tert-butoxide (LICKOR, 3.5 equiv.) in THF or benzene at 20–60 °C. The resulting dianion cyclizes to give the fluorenone skeleton. The metalation reactions of biphenyl-3- and -4-carboxylic acids are also described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)