Development of an efficient and Green protocols for C C and C Heteroatom bond formation employing organoboron reagents

Abstract

Abstract newlineA mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide(NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has beendeveloped. The addition of a catalytic amount of copper iodide found to promote rate enhancement ofthe iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid newlinewas observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis. newline