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Inne
N-acylcarbazoles and N-acylindoles: electronically activated amides for N–C(O) cross-coupling by Nlp to Ar conjugation switch.
Autorzy
Rok wydania
2020
Czasopismo
Numer woluminu
22
Strony
4703-4709
DOI
10.1021/acs.orglett.0c01488
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The development of new amide precursors for selective, catalytic activation of carbon–nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki–Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N–C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.
Słowa kluczowe
Amides, Molecular properties, Reactivity, Cross coupling reaction, Resonance structures
Adres publiczny
http://dx.doi.org/10.1021/acs.orglett.0c01488
Strona internetowa wydawcy
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