Book Review: Strategic applications of named reactions in organic synthesis

11 January 2019
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Title: Strategic applications of named reactions in organic synthesis - Background and detailed mechanisms

Author: Kurti, Laszlo | Czako, Barbara

Publisher: Academic Press, 2005

Reviewed By: Dr. Nikhat Farhana | Asst. Professor | School of Pharmacy

in 1979, A. Suzuki and N. Miyaura reported the stereoselective synthesis of arylated (E)-alkenes by the reaction of 1-alkenylboranes with aryl halides in the presence of a palladium catalyst. The palladium-catalyzed cross-coupling reaction between organoboron compounds and organic halides or triflates provides a powerful and general method for the formation of carbon-carbon bonds known as the Suzuki cross-coupling. There are several advantages to this method: 1) mild reaction conditions; 2) commercial availability of many boronic acids; 3) the inorganic by-products are easily removed from the reaction mixture, making the reaction suitable for industrial processes; 4) boronic acids are environmentally safer and much less toxic than organostannanes (see Stille coupling); 5) starting materials tolerate a wide variety of functional groups, and they are unaffected by water; 6) the coupling is generally stereo- and regioselective; and 7) sp3-hybridized alkyl boranes can also be coupled by the B-alkyl Suzuki-Miyaura cross-coupling. some disadvantages are: 1) generally aryl halides react sluggishly; 2) by-products such as self-coupling products are formed because of solvent-dissolved oxygen; 3) coupling products of phosphine-bound aryls are often formed; and 4) since the reaction does not proceed in the absence of a base, side reactions such as racemization of optically active compounds or aldol condensations occur.

Next is a detailed walk through of the detailed reaction mechanism. As can be seen in the figure below, the most elegant aspect of this book is the careful use of color. The reagents get their own colors, and new bonds formed are always black. This is especially useful in reactions undergoing rearrangement, like the Ugi reaction.

The second page of each entry is dedicated to demonstrations of the title reaction in synthetic applications. Several total syntheses are described with the step utilizing the named reaction highlighted. I like this aspect. It shows real-world applications and helps exemplify functional groups that tolerate the reaction conditions.

Each entry is extensively referenced, and even this is handled elegantly. The references are split into three (sometimes four) categories: Seminal Publications, Reviews, Modifications and Improvements, and sometimes Theoretical Studies. Several appendices at the back help your searching immensely. The first lists all the named reactions in the book in chronological order of their discovery. The next three appendices really help as they organize the reactions by reaction category (degradation, elimination, heterocycle formation…), reaction by affected functional group (from an alcohol, from a nitrile…), and reaction by target functional group (synthesis of epoxides, synthesis of oximes…)

This book is useful in many situations. The other day the name of the Cannizaro reaction escaped me.

Click here to view this title in KRRC OPAC


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