Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 7, Pages 2149-2153Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813887
Keywords
asymmetric catalysis; azole; C-H activation; ferrocene; regioselectivity
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Funding
- National Key R&D Program of China [2016YFA0202900]
- National Basic Research Program of China [2015CB856600]
- NSFC [91856201, 21572250, 21821002]
- Program of Shanghai Subject Chief Scientist [16XD1404300]
- CAS [XDB20000000, QYZDY-SSW-SLH012]
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Asymmetric C-H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C-H/C-H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C-H bond cleavage of azoles is likely proceeding through a SEAr process and may not be a turnover limiting step.
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