Carboxylate-directed kumada coupling of an acetaldehyde synthon with 2-bromobenzoates used towards the synthesis of isochromanes
(2007) Synlett : accounts and rapid communications in synthetic organic chemistry — n° 14, p. 2179-2184 (2007)
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- This letter describes the Kumada coupling of bromobenzoic acid derivatives with the acetaldehyde enolate synthon (1,3-dioxolan-2-ylinethyl)magnesium bromide. The lithium carboxylate salt shows the highest reactivity in the coupling reaction while addition of t-BuOLi affords optimal selectivity. During this work. we have observed a strong directing effect of the sodium carboxylate function which can be useful in differentiating electronically similar diaryl bromides.
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Houpis, L. N., Van Hoeck, J.-P., & Tilstam, U. (2007). Carboxylate-directed kumada coupling of an acetaldehyde synthon with 2-bromobenzoates used towards the synthesis of isochromanes. Synlett : accounts and rapid communications in synthetic organic chemistry, 14, 2179-2184. https://doi.org/10.1055/s-2007-985572 (Original work published 2007)