Palladium(II)-catalyzed oxidative dearomatization of free naphthols with two alkyne units.
Palladium(II)-catalyzed oxidative dearomatization of free naphthols with two alkyne units.
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DOI：
10.1021/ol502997d
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发表时间：
2014-11
期刊：
影响因子：
5.2
通讯作者：
Songlin Gu;Lei Luo;Jingjing Liu;Lu Bai;Huayu Zheng;Yaoyu Wang;X. Luan
中科院分区：
文献类型：
--
作者：
Songlin Gu;Lei Luo;Jingjing Liu;Lu Bai;Huayu Zheng;Yaoyu Wang;X. Luan
易得的2-萘酚在Pd(II)催化剂和氧化剂存在下与炔烃发生[2+2+1]螺环反应。这一过程依赖于2-萘酚1-位上的C-H官能化和萘环脱芳构化，从而得到各种螺环化合物。使用烷基-芳基-炔烃作为偶联对导致了区域异构体的混合物，有利于头尾异构体含有一个四元碳立体中心。
Readily available 2-naphthols undergo [2 + 2 + 1] spiroannulation reactions with alkynes in the presence of a Pd(II) catalyst and an oxidant. This process relies on C-H functionalization and naphthyl ring dearomatization at the 1-position of 2-naphthols to provide a variety of spirocyclic compounds. Using alkyl-aryl alkynes as the coupling partners led to regioisomeric mixtures in favor of the head-to-tail isomer bearing a quaternary carbon stereocenter.