A simple base-mediated halogenation of acidic sp2 C-H bonds under noncryogenic conditions.

A simple base-mediated halogenation of acidic sp2 C-H bonds under noncryogenic conditions.
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DOI:
10.1021/ol802411f
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发表时间:
2009-01-15
期刊:
影响因子:
5.2
通讯作者:
Daugulis, Olafs
Daugulis, Olafs
中科院分区:
化学1区
文献类型:
--
作者:
Do, Hien-Quang;Daugulis, Olafs

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开发了一种杂环和缺电子芳烃中酸性 sp2 碳氢键原位卤化的新方法。对于具有多个侧接吸电子基团的 C-H 键的底物,选择性单卤化或一步彻底多卤化都是可能的。对于大多数酸性芳烃,例如五氟苯,可以使用 K3PO4 碱代替 BuLi 进行金属化/卤化序列。
A new method has been developed for in situ halogenation of acidic sp2 carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K3PO4 base can be employed instead of BuLi for metalation/halogenation sequences.
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