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Palladium-Catalyzed Coupling of Propargylic Carbonates with N-Tosylhydrazones: Highly Selective Synthesis of Substituted Propargylic N-Sulfonylhydrazones and Vinylallenes

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An efficient palladium-catalyzed coupling of propargylic carbonates (1) with N-tosylhydrazones (2, 2′) has been carried out. A wide range of propargylic N-sulfonylhydrazones (3) and multisubstituted vinylallenes (4) can be obtained selectively by using either [PdCl2(CH3CN)2] or [Pd2(dba)3] as catalysts. (dba=trans,trans-dibenzylideneacetone, dppp=propane-l,3-diylbis(diphenylphosphane), Ts=4-toluenesulfonyl.)

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