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[Pd]-Catalyzed para-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols.

Sreenivasulu ChinnabattigallaAditya ChoudhurySatyanarayana Gedu
Published in: Organic & biomolecular chemistry (2021)
4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated from Dalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzed para-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.
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