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20.2.1.6.5.2 Variation 2: Carbolithiation–Carboxylation Sequence

DOI: 10.1055/sos-SD-020-00172

Evano, G.Science of Synthesis, (200720233.

Carbolithiation of alkenes is an excellent alternative to hydrometalation reactions. It allows for the direct introduction of an additional substituent during the 1,2-addition step, with complete atom economy.[‌143‌] Although the carbolithiation reaction of isolated or unstrained double bonds is rather limited, the addition of alkyllithium reagents to styrene derivatives has received a great deal of interest. An early example of the carbolithiationcarboxylation sequence is the reaction of norbornene with tert-butyllithium followed by trapping of the intermediate organolithium reagent 72 with carbon dioxide to give the carboxylic acid 73 (Scheme 27).[‌144‌]

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