Toward a better understanding on the mechanism of ortholithiation. Tuning of selectivities in the metalation of meta-anisic acid by an appropriate choice of base.

作者信息

Nguyen Thi-Huu, Chau Nguyet Trang Thanh, Castanet Anne-Sophie, Nguyen Kim Phi Phung, Mortier Jacques

机构信息

Unité de Chimie Organique Moléculaire et Macromoléculaire (UMR 6011), Faculté des Sciences, Université du Maine and CNRS, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.

出版信息

Org Lett. 2005 Jun 9;7(12):2445-8. doi: 10.1021/ol050761c.

DOI:10.1021/ol050761c

PMID:15932219

Abstract

[reaction: see text] If employed in THF at 0 degrees C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand. As a result of these findings, a new mechanism is proposed for the heteroatom-directed ortholithiation of aromatic compounds.

摘要