Alternative Synthesis of (Z)-1-Aryl-1-(tributylstannyl)-2-(triethylgermyl)ethenes and the Unprecedented Germyl 1,2-Migration during the Destannylation of the Adducts

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Abstract
A specific combination catalyst, Pd(dba)2 and 4-ethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, effectively catalyzed the addition of tributyl(triethylgermyl)stannane to arylacetylenes in tetrahydrofuran to give (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes in high yields. The (Z)-1-aryl-2-(germyl)-1-(stannyl)ethenes were subject to the unprecedented germyl 1,2-migration during the destannylation using HI / TBAI in toluene to produce 1-aryl-1-(germyl)ethenes in high yields.