Newsletter Issue 01 Jan-Feb 2008

Direct ortho Cupration: A New Route to Regioselectively Functionalized Aromatics

Directed ortho Metallation (DoM) is a widely spread method for the functionalization of aromatic compounds, working on many different substrates including heterocyclic ones. However, most applications of DoM involve the use of an organolithium base at low temperature, experimental conditions that make difficult the scale up of these reactions. A combined research by groups in Japan and United Kingdom offers now a new experimental protocol based in the use of Lipshutz-type amidocuprates. These amidocuprates are still prepared at low temperature from the usual starting materials (LiTMP, nBuLi and MeLi) but they offer higher regioselectivity than organolithium bases and less side reactions. The arylcopper intermediates can be succesfully used for trapping with several electrophiles.

J. Am. Chem. Soc. 129 (49), 15102-15103, 2007. See: 10.1021/ja074669i

GalChimia, S.L. Cebreiro s/n, 15823 O Pino (A Coruña) -  Spain Tel: +34 981 814 506 Fax: +34 981 814 507  www.galchimia.com