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Synlett 2024; 35(02): 240-244
DOI: 10.1055/a-2182-7532
DOI: 10.1055/a-2182-7532
letter
Diastereoselective Cross-Dehydrogenative Coupling Reactions of Amides with Diarylmethanes Using DDQ through Oxidative C–H Benzylic Activation
This work was supported by JSPS KAKENHI Grant Number JP20K05495.


Abstract
This study reports the chiral-auxiliary-controlled diastereoselective dehydrogenative coupling of diarylmethanes with amides by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone as the oxidant. The scope of the proposed reaction is very broad, with a wide variety of substrates and nucleophiles being applicable. The chiral induction can be attributed to the coordination of the oxygen atom on the chiral auxiliary with the carbocation intermediates.
Key words
amidation - chiral auxiliaries - C–H bond activation - dehydrogenation - diastereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2182-7532.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. August 2023
Angenommen nach Revision: 27. September 2023
Accepted Manuscript online:
27. September 2023
Artikel online veröffentlicht:
02. November 2023
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