Article: 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
[B]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[/B]
Thi-Huu Nguyen, Nguyet Trang Thanh Chau, Anne-Sophie Castanet, Kim Phi Phung Nguyen, and Jacques Mortier Org. Lett., 7 (12), 2445 -2448, 2005 [B]Abstract:[/B] If employed in THF at 0 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. [URL="http://chemvn.net/library/Chau%20Nguyet%20Trang%20Thanh/Toward%20a%20Better%20Understanding%20on%20the%20Mechanism%20of%20Ortholithiation%20-%20Tuning%20of%20Selectivities%20in%20the%20Metalation%20of%20meta-Anisic%20Acid%20by%20an%20Appropriate%20Choice%20of%20Base.pdf"]Download[/URL] |
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