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[Pd]-Catalyzed para-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2021-09-06 , DOI: 10.1039/d1ob01489g
Sreenivasulu Chinnabattigalla 1 , Aditya Choudhury 1 , Satyanarayana Gedu 1
Affiliation  

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.

中文翻译:

[Pd]-催化苯酚的对位选择性烯丙基化:获得 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

4-[( E )-3-Arylprop-2-enyl]酚是无所不在的支架,构成天然产物和具有生物学意义的化合物。钝角苯乙烯和钝角苯乙烯是从Dalbergia retusa中分离出来的两种基于酚类的天然产物。开发基于位点选择性烯丙基化的策略,特别是保护无基团的底物和非活化偶联剂,在有机合成中是必不可少的。在此,我们提出了一种高度区域选择性的 [Pd] 催化对位使用简单的、灭活的烯丙醇作为烯丙基化偶联物对酚进行-烯丙基化。值得注意的是,这种策略在露天和温和的反应条件下是成功的。此外, 本协议的有效性通过钝苯乙烯和钝苯乙烯的直接合成得到证明。
更新日期:2021-09-17
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