One‐Pot Synthesis of Functionalized 3‐(Trifluoromethyl)phenols by [3+3] Cyclization of 1,3‐Bis(silyl enol ethers) with α,β‐Unsaturated Trifluoromethyl Ketones

Abstract

Functionalized 3-(trifluoromethyl)phenols were prepared by formal [3+3] cyclization of 1,3-bis(silyl enol ethers) with readily available open-chained and cyclic α,β-unsaturated trifluoromethyl ketones. The reaction of 3,4-dihydro-5-(trifluo-

Synthesis of Fluorinated Arenes and Hetarenes Based on One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes

“…41 The TiCl 4 -mediated cyclization of 20 with 1,3-bis(silyloxy)-1,3-butadienes 4 afforded the novel 4-(2-furyl)-and 4-(2-thienyl)-6-(trifluoromethyl)salicylates 21 with very good regioselectivity (Scheme 9). The cyclization of dienes 4 with the methyl-substituted analogues of 20 proceeded with opposite regioselectivity.…”

Regioselective synthesis of CF2Cl-substituted biaryls by [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4-aryl-1-chloro-1,1-difluoro-4-(trimethylsilyloxy)-3-en-2-ones

“…These methods are limited with regard to scope and toxicity and availability of the required halogenation agents and aromatic substrates. In recent years, we developed the synthesis of various fluorinated arenes based on TiCl 4 -mediated [3?3] cyclizations of 1,3-bis (trimethylsilyloxy)-1,3-butadienes (for a review of [3?3] cyclizations, see [11]; for a review of 1,3-bis(silyl enol ethers), see [12]; [13][14][15][16][17][18]). Herein, we report, for the first time, the synthesis of 4-aryl-6-(chlorodifluoromethyl)salicylates by regioselective [3?3] cyclocondensation of various 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4-aryl-1-chloro-1,1-difluoro-4-(trimethylsilyloxy)-3-en-2-ones.…”

NMR Studies and Crystal Structure Determinations of CF3 Group-containing Bicyclic Phenolates

“…0932-0776 / 09 / 0400-0423 $ 06.00 c 2009 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com rated ketones [5]. This method provides an access to a class of compounds with a wide variety of substitution patterns depending on the educts being used.…”