ABSTRACT

The use of aluminum triphenolates such as 1 in toluene results in exclusive direct ortho-C-acylation with monochloroacetyl chloride. Indeed, the high coordinating ability of the metal can aid in promoting the formation of an organized reacting complex 2 that undergoes electrophilic attack to the proximate ortho position of the phenol ring, giving product 3 in 71% yield and 98% selectivity (Scheme 5.2).3