Science of Synthesis

Petit, C.; Montchamp, J.-L., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 331.

General Introduction

Organophosphorus compounds have a broad range of applications in a variety of chemical fields, including supporting ligands for metal catalysts, extractants, flame retardants, materials such as metal-organic frameworks, synthetic intermediates and reagents, and biologically active compounds for medicine and agrochemistry. As a result, methods for the formation of C—P bonds continue to be extremely important in chemical synthesis. This chapter specifically covers C—P bond formation via metal-catalyzed cross coupling between a variety of phosphorus compounds and electrophiles containing aryl sp2 carbons. Although methods applying to aryl sp2 carbons often also apply to alkenyl sp2 carbons, this will not be discussed in detail here because of space limitation and the fact that alkenylphosphorus compounds can often be more easily obtained by other methods that do not require the prior synthesis of the requisite alkenyl electrophile, such as alkenation of carbonyl compounds or metal-catalyzed addition to alkynes. Recent reviews covering related reactions of various phosphorus-containing functional groups are available.[‌1‌–‌14‌]

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References