The preparation of N-methyliminodiacetic acid protected alkynyl boronates

Abstract

The purpose of this work is to document the attempted syntheses of N-methyliminoacetic acid (MIDA) -protected alkynyl boronates according to procedures and methodologies that have been successfully employed in the syntheses of MIDA-protected alkyl, alkenyl, aryl and heteroaryl boronates. The rationale for the development of this class of MIDA-protected boronates is presented, both in terms of some of the more synthetically useful boronic acid reactions, which would demonstrate the desirability of the inclusion of the boronic functionality in the molecule, and in terms of the alkynyl functionality and its synthetic utility. This was done to show the potential synthetic utility and versatility of these MIDA-protected boronates. The synthetic approaches to these desirable compounds are presented. The results of each of these synthetic approaches are examined, and potential shortcomings and errors in each approach are identified. New synthetic approaches and potential experiments are identified that may be successful in the goal of successful syntheses of these potentially valuable synthetic building blocks.