A novel palladium(0) catalysed hydro-alkylation or –alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to involve the in situ formed t-butanol as proton source in the key step of the allylpalladium(II) species generation. Moreover, lithium iodide or iodobenzene are employed as an unprecedented iodide (I-) reservoir to sustain the catalytic cycle.
Cooperative Iodide Pd(0) Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: a Selective Synthesis of Conjugated and Skipped Dienes
Parisotto Stefano;PALAGI, LORENZO;Prandi Cristina;Deagostino Annamaria
2018-01-01
Abstract
A novel palladium(0) catalysed hydro-alkylation or –alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to involve the in situ formed t-butanol as proton source in the key step of the allylpalladium(II) species generation. Moreover, lithium iodide or iodobenzene are employed as an unprecedented iodide (I-) reservoir to sustain the catalytic cycle.
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