Hypervalent iodine mediated para-selective fluorination of anilides.

The Journal of organic chemistry (2012-12-12)
Tian Tian, Wen-He Zhong, Shuai Meng, Xiang-Bao Meng, Zhong-Jun Li
ABSTRACT

A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)(2)) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Hydrofluoric acid, ACS reagent, 48%
Sigma-Aldrich
Iodobenzene, 98%
Sigma-Aldrich
Hydrofluoric acid, 48 wt. % in H2O, ≥99.99% trace metals basis
Sigma-Aldrich
Hydrofluoric acid, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥48%
Sigma-Aldrich
Hydrofluoric acid, puriss. p.a., reag. ISO, reag. Ph. Eur., ≥40%