Preparation of MIDA Anhydride and Reaction with Boronic Acids

Author:

Chen Peng‐Jui,Kelly Aidan M.,Blair Daniel J.,Burke* Martin D.

Abstract

Abstract This chapter describes the procedure for preparation of N ‐methyliminodiactic acid (MIDA) anhydride and reaction with boronic acids. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards. Boronic acids are amongst the most widely used reagents for the assembly of small organic molecules. The protection of boron with MIDA has broadly enabled the synthesis of many complex MIDA boronate building blocks using transformations otherwise incompatible with boronic acids. MIDA boronates possess an unusual binary affinity for silica gel.

Publisher

Wiley

Reference66 articles.

1. The authors gratefully acknowledge the NIH (GM118185). D.J.B. is an Illini 4000 Post‐Doctoral Fellow of the Damon Runyon Cancer Research Foundation (DRG‐2290–17). Mailing address: 454 Roger Adams Laboratory 600 S. Mathews Avenue Department of Chemistry University of Illinois at Urbana‐Champaign mdburke@illinois.edu. (ORCID: 0000‐0001‐7963‐7140)

2. Selection of boron reagents for Suzuki–Miyaura coupling

3. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis

4. Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries

5. Protodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH–Rate Profiles, Autocatalysis, and Disproportionation

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