Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 11, Pages 5843-5847Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016009
Keywords
asymmetric catalysis; C-H borylation; chiral amines; organoboron compounds; pyrazoles
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Funding
- National Natural Science Foundation of China [21801246, 91956116]
- Natural Science Foundation of Jiangsu Province [BK20170422]
- Hangzhou Normal University [KFJJ2021001]
- Lanzhou Institute of Chemical Physics
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This study presents a pyrazole-directed iridium-catalyzed enantioselective borylation of unbiased methylene C-H bonds at the position beta to a nitrogen center, providing high regio- and enantioselectivity. The method is capable of tolerating a wide range of functional groups, yielding C(sp(3))-H functionalization products with good to excellent enantioselectivity.
Reported herein is the pyrazole-directed iridium-catalyzed enantioselective borylation of unbiased methylene C-H bonds at the position beta to a nitrogen center. The combination of a chiral bidentate boryl ligand, iridium precursor, and pyrazole directing group was responsible for the high regio- and enantioselectivity observed. The method tolerated a vast array of functional groups to afford the corresponding C(sp(3))-H functionalization products with good to excellent enantioselectivity.
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