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6.1.38.25.2 Variation 2: Carbonylative Cross Coupling of Trialkylboranes and Acyl–Alkyl Coupling

DOI: 10.1055/sos-SD-006-00903

Zaidlewicz, M.; Krzeminski, M.Science of Synthesis, (200561187.

Carbon monoxide inserts into the PdC bond preventing alkene formation; consequently, carbonylative coupling of alkylboranes with alkyl iodides affords unsymmetrical ketones in good yields.[‌545‌] Primary, secondary, and tertiary iodoalkenes can be carbonylated and cross coupled with 9-alkyl-9-bora[3.3.1]bicycloboranes. The use of iodides is essential for achieving high yields, since organic bromides undergo competitive transmetalation with organoboranes, resulting in lower yields of ketones. Various ketones and functional derivatives have been prepared by this methodology, including the ester 93 (Scheme 161).[‌546‌]

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