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Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-01-16 , DOI: 10.1002/anie.201913388
Xingxing Liu 1, 2 , Qing Zhu 2, 3 , Du Chen 2, 3 , Lu Wang 2 , Liqun Jin 1 , Chao Liu 2, 4
Affiliation  

The aminoazanium of DABCO (H2 N-DABCO) has been developed as a general and practical amination reagent for the direct amination of alkyl and aryl pinacol boronates. This compound is stable and practical for use as a reagent. Various primary, secondary. and tertiary alkyl-Bpin and aryl-Bpin substrates were aminated to give the corresponding amine derivatives. The amination is stereospecific. The anti-Markovnikov hydroamination of olefins was easily achieved by catalytic hydroboration with HBpin and in subsequent situ amination using H2 N-DABCO. Moreover, the combination of 1,2-diboration of olefins, using B2 pin2 , with this amination process achieved the unprecedented 1,2-diamination of olefins. The amination protocol was also successfully extended to aryl pinacol boronates.

中文翻译:

DABCO的氨基氮杂:烷基和芳基品那可硼酸酯的胺化试剂。

已经开发了DABCO(H2 N-DABCO)的氨基氮杂作为直接和胺化频哪醇硼酸烷基酯的通用和实用的胺化试剂。该化合物是稳定且实用的试剂。各种小学,中学。将叔烷基-Bpin和芳基-Bpin底物胺化,得到相应的胺衍生物。胺化是立体定向的。通过用HBpin催化加氢硼化并随后使用H2 N-DABCO进行原位胺化,可以轻松实现烯烃的抗马氏复合氢化。此外,使用B2 pin2将烯烃的1,2-二硼化与这种胺化工艺相结合,实现了前所未有的烯烃1,2-醛化。胺化方案也成功地扩展到芳基频哪醇硼酸酯。
更新日期:2020-01-16
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