Direct Superacid‐Promoted Difluoroethylation of Aromatics
Under superacid conditions, aromatic amines are directly and regioselectively 1,1‐difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α‐fluoronium and α‐chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be appli...
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Published in | Chemistry : a European journal Vol. 28; no. 6; pp. e202103926 - n/a |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
27.01.2022
Wiley Subscription Services, Inc Wiley-VCH Verlag |
Subjects | |
Online Access | Get full text |
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Summary: | Under superacid conditions, aromatic amines are directly and regioselectively 1,1‐difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α‐fluoronium and α‐chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late‐stage functionalization of natural alkaloids and active pharmaceutical ingredients.
Through an original superelectrophile‐promoted difluoroethylation in superacid, CF2‐Me aromatic amines can be synthesized directly and regioselectivity. Applied to simple substrates, natural alkaloids and active pharmaceutical ingredients, this method offers an alternative for the late‐stage synthesis of aryl methyl ethers bioisosters. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.202103926 |