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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.

Organic letters (2005-06-04)
Thi-Huu Nguyen, Nguyet Trang Thanh Chau, Anne-Sophie Castanet, Kim Phi Phung Nguyen, Jacques Mortier
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
3-Methoxybenzoic acid, ReagentPlus®, 99%
Sigma-Aldrich
m-Anisic acid, ≥98%