(1-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

• Published in: Tetrahedron Vol. 69; no. 36; pp. 7732 - 7740
• Main Authors: Woerly, Eric M., Miller, Jonathan E., Burke, Martin D.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.09.2013; Elsevier
• Subjects: 1,1-Disubstituted boronates; 1,1-Disubstituted olefins; Accessibility; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Construction; Cross coupling; Iterative cross-coupling; MIDA boronates; organic compounds; Physical Sciences; Platforms; Science & Technology; Synthesis; Tetrahedrons; 1,1-Disubstituted olefins; Iterative cross-coupling; 1,1-Disubstituted boronates; MIDA boronates; GENERAL-SOLUTION; ACID; OLEFIN CROSS-METATHESIS; TERMINAL ALKYNES; BIS(PINACOLATO)DIBORON; ARYL HALIDES; HECK REACTION; EFFICIENT; DERIVATIVES; 1,1-DIARYLETHYLENES; 1,1-disubstituted olefins; 1,1-disubstituted boronates
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2013.05.050

Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (1-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as a starting material for the preparation of a wide range of 1,1-disubstituted olefin-containing MIDA boronates. This compound can also be used for the iterative cross-coupling-based synthesis of various 1,1-disubstituted olefin-containing targets. Collectively, these results contribute to the expanding generality of the MIDA boronate platform. [Display omitted]