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26.9.1.1.3.7 Variation 7: Transition-Metal-Catalyzed Coupling of Alkenylmetals with Organic Halides and Carbon Monoxide

DOI: 10.1055/sos-SD-026-00987

Marsden, S. P.Science of Synthesis, (2005261057.

An alternative approach to the synthesis of acylpalladium(II) species for cross couplings involves the carbonylation of aryl- or alkenylpalladium(II) complexes generated from insertion of palladium(0) into the corresponding organic halide or equivalent. The main advantage of this protocol is that it allows the coupling of components bearing functionality such as primary amines which would not be tolerated in the acid chloride based approach. The reaction works with a variety of both electrophilic and nucleophilic components, as exemplified by the coupling of aromatic iodide 58 with alkenylaluminum 59,[‌58‌] the preparation of enone 62 by reaction of aryl trifluoromethanesulfonate 60 with alkenylstannane 61,[‌59‌] and reaction of benzenediazonium salt 63 with vinylboronic acid 56 to yield 57 (Scheme 14).[‌60‌]

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