Iterative Suzuki Miyaura Coupling Reaction

Iterative Suzuki Miyaura Coupling Reactions

     The Suzuki-Miyaura cross-coupling reaction of boronic acids is one of the most important and highly utilized reactions in the organic chemistry toolbox, with applications in polymer science as well as in the fine chemicals and pharmaceutical industries. However, many boronic acids are extremely unstable and susceptible to decomposition that renders them inefficient in coupling reactions or makes long-term storage difficult.

    Iteration (lat. “iterare”=to repeat) is a powerful strategy employed in the biosynthesis of complex molecules. In these controlled iterative reactions, di- and multifunctional building blocks are employed that contain only one reactive functional group (“ON”), while all other groups are unreactive (“OFF”) thereby suppressing uncontrolled polymerization (Scheme 1). After the selective coupling of the reactive group, another, previously unreactive functional group is activated/deprotected (“ON”) and the coupling sequence repeated, thus allowing the efficient formation of defined oligomers from readily available building blocks. This enables even nonexperts to synthesize complex molecules in a short time, and promotes the rapid investigation and application of these compounds in chemistry and biology. An ideal iterative coupling would meet the following criteria:

ü  Many differently substituted building blocks are readily available and inexpensive;

ü  Coupling and activation/deprotection step are high yielding, are tolerant of many different functional groups, and do not require nor produce toxic compounds;

ü  Handling, separation, and purification are facile;

ü  The iterative coupling sequence is reliable and predictable, which are important aspects for applications in natural product synthesis and in industry;

ü  The sequence is suitable for solid phase synthesis and automation.

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