Water works: an efficient palladium-catalyzed cross-coupling reaction between boronic acids and bromoacetate with aminophosphine ligand

Pd-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with 2-Chloroacetates and 2-Chloroacetamides

“…13 Good yields were achieved in this study, but only ( E )-alkenylboronic acids were evaluated, none of which provided any evidence of functional group compatibility. Although alkenylboronic acids are efficient substrates and solve many of the prevailing limitations in the synthesis of β,γ-unsaturated carbonyl compounds, they suffer disadvantages related to the instability of alkenylboronic acids.…”

“…Additionally, the cross-coupling of α-bromoacetates with alkenylboronic acids has recently been investigated . Good yields were achieved in this study, but only ( E )-alkenylboronic acids were evaluated, none of which provided any evidence of functional group compatibility.…”

“…14 Furthermore, the use of a large excess (20 mol %) of the boronic acid partner is usually necessary to obtain good yields of desired product. 13 …”

“…These compounds exhibit a tendency to polymerize readily, which is especially prevalent in low molecular weight examples such as vinyl and propenylboronic acids . Furthermore, the use of a large excess (20 mol %) of the boronic acid partner is usually necessary to obtain good yields of desired product …”