CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION
CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION
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DOI：
10.1021/ja00767a072
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发表时间：
1972-01-01
影响因子：
15
通讯作者：
GUPTA, SK
中科院分区：
文献类型：
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作者：
BROWN, HC;GUPTA, SK
最近的研究发现了几种新的反应，揭示了烯基硼烷3和烯基硼酸酯和酸4在有机合成中日益重要。烯基硼烷可通过用硼烷2及其烷基衍生物处理炔来获得。3.然而，目前还没有合成烯硼酸和酯的方便的通用方法。例如，有机金属试剂已用有机硼酸盐处理，得到简单的、功能上未取代的链烯硼酸和酯。4· 5 Zweifel等人开发了一种两步法，包括用二环己基硼烷对炔进行硼氢化，然后对所得烯基二烷基硼烷进行选择性氧化（等式6）。炔的硼氢化反应
Recent investigations have led to the discovery of several new reactions which reveal the increasing im-portance of alkenylboranes3 and alkeneboronic esters and acids4 in organic synthesis. The alkenylboranes are available via the treatment of alkynes with borane2 and its alkyl derivatives. 3 A convenient, general pro-cedure for the synthesis of alkeneboronic acids and esters, however, is presently not available. Organome-tallic reagents, for example, have been treated with or-ganic borates to give simple, functionally unsubstituted alkeneboronic acids and esters. 4· 5 A two-step pro-cedure involving the hydroboration of alkynes with dicyclohexylborane followed by theselective oxidation of the resultingalkenyldialkylborane has been developed by Zweifel, et alf (eq 6). The hydroboration of alkynes