Formation of pinacol boronate esters via pyridine iodoborane hydroboration.

Formation of pinacol boronate esters via pyridine iodoborane hydroboration.
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通过吡啶碘硼烷硼氢化形成频哪醇硼酸酯。

DOI:
10.1021/jo8020049
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发表时间:
2008
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Vedejs,Edwin
Vedejs,Edwin
中科院分区:
--
文献类型:
--
作者:
Karatjas,AndrewG;Vedejs,Edwin

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用吡啶碘硼烷对烯烃进行硼氢化反应,再用萘酚/氢氧化钠处理,得到产率中高的单烷基硼萘酚酯。二基硼酸衍生物是竞争性形成的,尤其是末端烯烃。这种副反应可以通过使用过量的吡啶碘硼烷来最小化。越受阻的烯烃反应效果越好。
Hydroboration of alkenes with pyridine iodoborane followed by treatment with pinacol/NaOH affords monoalkyl pinacol boronates in moderate to good yield. Dialkylborinic acid derivatives are formed competitively, especially in the case of terminal alkenes. This side reaction can be minimized by using excess of pyridine iodoborane. More hindered alkenes give the best results.