Cross-coupling allylation

Allyl-allyl cross-coupling of allyl bromides (Structure 1) and allyl sulfides (2) carrying homoallylic alcohol or ester functions takes place under irradiation with hexamethylditin (see eq. (1)). The reaction cleanly leads to 2,6-dienes (3) and no isomerization of allylic bromides is oberserved [56]. 

Scheme 10.149 Synthesis of functionalized fused sulfur heterocycles by intramolecular carbometallation of alkynylaryl thioethers/allylation/cross-coupling [123].

Homillos V, P6rez M, Fananas-Mastral M, Feringa BL (2013) Copper-catalyzed enantioselective allyl-allyl cross-coupling. J Am Chem Soc 135 2140-2143... 

Hojoh K, Shido Y, Ohmiya H, Sawamura M (2014) Construction of quaternary stereogenic carbon centers through copper-catalyzed enantioselective allylic cross-coupling with alkylboranes. Angew Chem Int Ed 53 4954-4958... 

Katzenellenbogen, J. A., and R. S. Lenox The generation of allyllithium reagents by lithium-tetrahydrofuran reduction of allylic mesitoates. A new procedure for selective allylic cross coupling and allylcarbinol synthesis. J. Org. Chem. 38, 326—335 (1973). 

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