Investigation of alkyne regioselectivity in the ni-catalyzed benzannulation of cyclobutenones.
Investigation of alkyne regioselectivity in the ni-catalyzed benzannulation of cyclobutenones.
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DOI：
10.1002/chem.201405863
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发表时间：
2015-02
期刊：
影响因子：
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通讯作者：
T. Stalling;W. Harker;A. Auvinet;E. J. Cornel;J. Harrity
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文献类型：
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作者：
T. Stalling;W. Harker;A. Auvinet;E. J. Cornel;J. Harrity
环丁烯酮和炔烃的镍催化苯并环化反应可快速合成重取代酚。该反应的区域选择性可以通过改变炔烃上的取代基来调节。尽管路易斯碱性供体的掺入提供了适度的选择性，但芳基取代基的使用可以提供高水平的区域控制。最后，由烷基取代的乙炔衍生的炔基硼酸酯提供高产率和区域选择性。这项研究表明，带有一个 sp(2) 和一个 sp(3) 基取代基的炔烃可以进行苯并环化，并具有高水平的区域控制，其中 sp(3) 基基团与酚 OH 邻位结合。
A Ni-catalyzed benzannulation reaction of cyclobutenones and alkynes provides a rapid synthesis of heavily substituted phenols. The regioselectivity of this reaction can be modulated by variation of substituents on the alkyne. Though the incorporation of Lewis basic donors provides modest selectivities, the use of aryl substituents can provide high levels of regiocontrol. Finally, alkynylboronates derived from alkyl-substituted acetylenes provide both high yields and regioselectivities. This study suggests that alkynes bearing one sp(2) - and one sp(3) -based substituent can undergo benzannulation with high levels of regiocontrol whereby the sp(3) -based group is incorporated ortho-to the phenolic OH.