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21.4.3.1.1 Method 1: Copper(I)-Catalyzed Coupling of Amides and Vinyl Iodides with Copper(I) Thiophenecarboxylate

DOI: 10.1055/sos-SD-021-00318

Tracey, M. R.; Hsung, R. P.; Antoline, J.; Kurtz, K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y.Science of Synthesis, (200521416.

The synthesis of enamides can be achieved via a copper(I)-catalyzed coupling of vinyl iodides and amides. In some cases the products are the starting materials for macrolides.[‌74‌] An example of this type of coupling reaction is shown in Scheme 44 where (2E,4E)-N-[(1E)-hept-1-en-1-yl]hexa-2,4-dienamide (86), can be obtained from the amide 84 and the iodide 85 using copper(I) thiophene carboxylate (CuTC) as the coupling agent. This methodology is used in the syntheses of antitumor natural products bearing an enamide side chain, such as the lobatamides AF,[‌75‌,‌76‌] oximidines IIII,[‌77‌,‌78‌] and CJ-12,950.[‌79‌]

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