trans-2-Bromovinylboronic acid MIDA ester

Burke and coworkers recently prepared retinal using newly-developed methodology, which employs boronic acid surrogates, termed MIDA boronates (retinal synthesis employed key MIDA building block BB1—S...
Dr. Josephine Nakhla
Chemfiles Volume 10 Article 1
Keywords: Building blocks, Catalog, Coupling reactions, Cross couplings, Solvents

Professor Martin Burke and coworkers recently prepared retinal using key MIDA building block BB1 in iterative Suzuki-Miyaura cross coupling reactions (Scheme 1). The MIDA unit of BB1 is unreactive un...
Aaron Thornton
ChemFiles Volume 11 Article 1
Keywords: Building blocks, Coupling reactions, Cross couplings, Solvents

The Suzuki-Miyaura cross-coupling reaction is one of the most important and highly utilized reactions in organic chemistry, with applications in polymer science as well as in the fine chemicals and p...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Aminations, Bromoborations, Building blocks, Catalysis, Chromatography, Coupling reactions, Cross couplings, Cross metathesis, Cyclopropanations, Epoxidations, Industries, Ligands, Metathesis, Natural product synthesis, Olefin metathesis, PAGE, Pharmaceutical, Polymer science, Protocol, Purification, Reductions, Reductive aminations, Stille coupling, Suzuki coupling, Suzuki reactions, Takai olefination, Transmetalation, transformation

Due to the instability of some boronic acids, the Burke group has developed very practical syntheses of some of the more challenging MIDA boronates. For instance, while trans-(2-bromovinyl) MIDA boro...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Bromoborations, Building blocks, Transmetalation

Palladium-catalyzed cross-coupling reactions are ideal methods for the synthesis of polyenes because of the stereospecificity of the reactions and the mildness of the reaction conditions. However, po...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Building blocks, Catalysis, Coupling reactions, Cross couplings, Natural product synthesis, Suzuki reactions

The utility of vinyl MIDA boronate was demonstrated via cyclopropanation and epoxidation to the corresponding MIDA cyclopropane and oxirane, respectively. These procedures (Scheme 13) provided air an...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Chromatography, Cross metathesis, Cyclopropanations, Epoxidations, Metathesis, Olefin metathesis, Purification, transformation

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 a...

MIDA boronates are stable boronic acid surrogates used for Suzuki-Miyaura cross-coupling reactions. These reagents enable the coupling of historically unstable organoboron species; including those co...