Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.
Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.
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DOI：
10.1021/jo051948k
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发表时间：
2006-01
期刊：
影响因子：
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通讯作者：
Xiaoxiang Zhang;Sampa Sarkar;R. Larock
中科院分区：
文献类型：
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作者：
Xiaoxiang Zhang;Sampa Sarkar;R. Larock
[反应：在温和的反应条件下，通过合适的含芳烃炔丙醇与ICl、I2、Br 2、NBS和PhSeBr的6-内切-二氢亲电环化反应，容易地区域选择性地制备各种取代的萘。3-碘-2-萘酚也可以通过类似的1-芳基-3-炔-2-酮的环化反应以优异的产率制备。这种方法很容易容纳各种官能团，并已成功地扩展到取代的咔唑和二苯并噻吩的合成。
[reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.