N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N–C(O) Cross-Coupling by Nlpto Ar Conjugation Switch
In: Organic Letters, Jg. 22 (2020-06-19), Heft 12, S. 4703-4709
Online
serialPeriodical
Zugriff:
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 Nlpto 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.
Titel: |
N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N–C(O) Cross-Coupling by Nlpto Ar Conjugation Switch
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Autor/in / Beteiligte Person: | Buchspies, Jonathan ; Rahman, Md. Mahbubur ; Szostak, Roman ; Szostak, Michal |
Link: | |
Zeitschrift: | Organic Letters, Jg. 22 (2020-06-19), Heft 12, S. 4703-4709 |
Veröffentlichung: | 2020 |
Medientyp: | serialPeriodical |
ISSN: | 1523-7060 (print) ; 1523-7052 (print) |
DOI: | 10.1021/acs.orglett.0c01488 |
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