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20.2.10.1.1.1 Variation 1: Friedel–Crafts Carboxylation

DOI: 10.1055/sos-SD-020-00506

Yoon, T. P.; Jacobsen, E. N.Science of Synthesis, (200720533.

Carbonylation of arenes can be accomplished by acylation with phosgene in the presence of a Lewis acid catalyst; the resulting acid chloride is hydrolyzed to provide a carboxylic acid such as benzoic acid (1) (Scheme 1).[‌3‌] However, the intermediate acid chloride can sometimes undergo reaction with a second equivalent of arene, and quite often the major product isolated from these reactions is a diaryl ketone rather than the desired acid. The use of less-reactive phosgene equivalents such as oxalyl chloride minimizes this side reaction and avoids the use of toxic phosgene gas. Recently, it has been shown that carboxylation of arenes can be effected directly using carbon dioxide.[‌4‌] The reaction is performed under high pressure in the presence of aluminum trichloride and aluminum metal.

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