Modulation of the Electronic Properties of Non-innocent (E,E)-Dibenzylideneacetone for Palladium(0)-Mediated Heck Alkenylation of 5-Iodo-2′-deoxyuridine and Scale-Up Studies

Dedicated to Professor Richard K. Taylor on his 65^th birthday

Abstract

Subtle modulation of the electronic properties of the dibenzylideneacetone (dba) ligand allows the development of an efficient protocol for the Heck alkenylation of 5-iodo-2′-deoxyuridine. This protocol enables the large-scale synthesis of commercially important nucleoside building blocks. The isolation of one key molecule was accomplished under column-free conditions on a 10-gram scale.

Key words

Heck alkenylation - dibenzylideneacetone - scale-up - nucleosides - 5-iodo-2′-deoxyuridine

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