Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium‐catalyzed hydroboration of aliphatic internal alkenes, providing distal‐borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate...

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Bibliographic Details
Published in:Angewandte Chemie 2019-06, Vol.131 (24), p.8271-8275
Main Authors: Wang, Guangzhu, Liang, Xinyi, Chen, Lili, Gao, Qian, Wang, Jian‐Guo, Zhang, Panke, Peng, Qian, Xu, Senmiao
Format: Article
Language:English
Subjects:
Aliphatic compounds
Alkene
Alkenes
Alkylboronsäuren
Chemistry
Functional groups
Hydroboration
Hydroborierung
Iridium
Regioselectivity
Synthesemethoden
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Summary:The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium‐catalyzed hydroboration of aliphatic internal alkenes, providing distal‐borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal‐borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle. Der leicht zugängliche Katalysator [Cp*IrCl2]2 ermöglicht die Hydroborierung nichtaktivierter interner Alkene unter milden Reaktionsbedingungen. In dieser Reaktion werden viele funktionelle Gruppen toleriert und verschiedenste distal borylierte Produkte mit einer Regioselektivität bis zu 99 % erhalten. Aufgrund von Dichtefunktionalrechnungen wird ein IrIII/IrV‐Cyclus vorgeschlagen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201902464