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2.7.1 C—C Cross-Coupling Reactions of Acidic C—H Nucleophiles with One Activating Group

DOI: 10.1055/sos-SD-208-00380

Marsden, S. P.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132565.

General Introduction

The α-aryl carbonyl functionality is found in a wide range of important synthetic and naturally occurring biologically active molecules (Scheme 1). The α-aryl ketone motif, for example, occurs twice in the natural product gustastatin (1), while the alkaloid atropine (2) contains an α-aryl ester group. α-Aryl carboxylic acids are widely found in synthetic nonsteroidal anti-inflammatory drugs such as diclofenac (3) and the family of arylpropanoic acids exemplified by naproxen (4). The antihypertensive verapamil (5) contains an α-aryl alkanenitrile grouping. Additionally, the rich chemistry of carbonyl and carboxylate functional groups means they also serve as key building blocks for elaboration into an even broader range of valuable targets. As such, ready access to this functionality in an efficient and selective manner, using convenient and widely available starting materials, is an important synthetic tool.

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References


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