Boronic Acids: Preparation and Applications in Organic

Following the large good fortune of the 1st version, which has turn into THE reference resource for everybody operating within the box, this long-awaited, thoroughly up-to-date version positive aspects nearly 50% new content.
The world-renowned chemist Prof Dennis corridor is joined by means of a choose crew of most sensible authors to hide all sleek facets of boronic acid derivatives in a single entire guide. The experimental tactics defined make for terribly precious analyzing.
From the studies of the 1st variation: "...deserves to be at the bookshelf of all artificial chemists, even if in discovery or procedure chemistry."

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Additional info for Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2), Second Edition

Sample text

Boronic esters also react to give the desired salts [127]. These crystalline derivatives are easy to handle, are competent substrates in many of the same reactions that employ free boronic acids, and often outperform boronic acids as cross-coupling reagents. Chapter 11 provides an overview of their synthetic applications in transition metal cross-coupling reactions and other transformations [194]. They have also been evaluated as tracer molecules for positron emission tomography (PET) applications [195].

Amino acids can condense with boronic acids to form 1 : 1 chelates of type 67 [173]. The tetracoordinate structure of these adducts is very apparent by NMR due to the formation of a new stereocenter at boron. 17) [174]. This dimer is prevalent at low concentrations (<50 mM), while oligomeric mixtures predominate at higher concentrations. Amino acid adducts of boronic acids are hydrolytically unstable, and 69 was indeed found to revert to free 68 upon addition of water to the solution. 17) is stable [24].

7). Indeed, based on 11 B NMR and UV spectroscopic evidence, it was suggested that 18 acts as a Brønsted acid in water and forms conjugate base 19A through direct proton transfer [71]. A small number of other boronic acids are suspected of behaving as Brønsted acids due to the same reasons [72]. 2 Bimolecular Lewis Acid–Base Complexation under Nonaqueous Conditions As evidenced by the high pH required in the formation of boronate anions, boronic acids and most dialkyl esters are weak Lewis acids.

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