3-Bromo-2-t-butylsulfonyl-1-propene.a versatile multi-coupling reagent part 1

Add time:07/20/2019    Source:sciencedirect.com

The 3-bromo-2-t-butylsulfonyl-1-propene 3 was prepared in two steps from allyl-t-butylthioether in 70% overall yield. This reagent reacts selectively with a broad range of nucleophiles (amine, thiolate, lithium ester- and keto- enolates, magnesium, zinc and lithium organomatallics) to furnish the unsaturated sulfones of type 4 in typical yields of 80–90%. The sulfone 3 reacts also in the presence of zinc with various electrophiles (aldehydes, ketonos, nitriles and an imine) to afford the functionalized unsaturated sulfones of type 7 in good yields.

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