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用二异丁基-丁氧基氢化铝锂催化的频哪醇硼烷对烯烃进行硼氢化反应。

Alkene hydroboration with pinacolborane catalysed by lithium diisobutyl--butoxyaluminum hydride.

作者信息

Jaladi Ashok Kumar, Shin Won Kyu, An Duk Keun

机构信息

Department of Chemistry, Institute for Molecular Science and Fusion Technology, Kangwon National University Chunchon 24341 Republic of Korea

出版信息

RSC Adv. 2019 Aug 23;9(45):26483-26486. doi: 10.1039/c9ra04699b. eCollection 2019 Aug 19.

DOI:10.1039/c9ra04699b
PMID:35530999
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9070384/
Abstract

Here we developed a highly efficient alkene hydroboration protocol, showing that various alkyl boronates can be smoothly obtained in good yields by reacting alkenes with pinacolborane (HBpin) in the presence of 5 mol% lithium diisobutyl--butoxyaluminum hydride. The coordination of aluminate ions with lithium cations allowed for effective hydride transfer during hydroboration, and the obtained boronate ester was further used for C-C coupling, trifluoroboronate salt formation, and oxidation to alcohol.

摘要

在此,我们开发了一种高效的烯烃硼氢化反应方案,结果表明,在5 mol%的二异丁基-丁氧基氢化铝锂存在下,烯烃与频哪醇硼烷(HBpin)反应能够顺利地以良好产率得到各种硼酸烷基酯。铝酸根离子与锂阳离子的配位作用使得硼氢化反应过程中能够有效地进行氢化物转移,并且所得到的硼酸酯进一步用于碳-碳偶联、三氟硼酸盐的形成以及氧化为醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/c20d6fd50de6/c9ra04699b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/8319f2738e94/c9ra04699b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/6be7ad35155b/c9ra04699b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/15cfa26ff3d0/c9ra04699b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/c20d6fd50de6/c9ra04699b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/8319f2738e94/c9ra04699b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/6be7ad35155b/c9ra04699b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/15cfa26ff3d0/c9ra04699b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/142b/9070384/c20d6fd50de6/c9ra04699b-s3.jpg

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