Palladium-catalyzed cross coupling reaction of N-alkoxyimidoyl bromides and its application to one-pot synthesis of N-arylamines
- PMID: 21881275
- DOI: 10.1248/cpb.59.1206
Palladium-catalyzed cross coupling reaction of N-alkoxyimidoyl bromides and its application to one-pot synthesis of N-arylamines
Abstract
The synthetic utility of N-alkoxyimidoyl halides is demonstrated using the palladium-catalyzed cross-coupling reaction. The Sonogashira and Suzuki-Miyaura coupling reactions of N-alkoxyimidoyl bromides produced versatile ketoxime ethers in good to excellent yields. A one-pot reaction of the imidoyl bromides with arylboronic acid and allylmagnesium bromide to produce N-arylamines via Suzuki-Miyaura coupling followed by domino reaction involving sequential addition-eliminative rearrangement-addition reactions was developed.
Similar articles
-
Stereospecific Suzuki, Sonogashira, and Negishi coupling reactions of N-alkoxyimidoyl iodides and bromides.J Org Chem. 2013 Apr 19;78(8):3676-87. doi: 10.1021/jo400179u. Epub 2013 Apr 11. J Org Chem. 2013. PMID: 23534335
-
Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation.J Am Chem Soc. 2011 May 11;133(18):6948-51. doi: 10.1021/ja201743j. Epub 2011 Apr 19. J Am Chem Soc. 2011. PMID: 21504197
-
Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines.J Am Chem Soc. 2009 Aug 12;131(31):11049-61. doi: 10.1021/ja903049z. J Am Chem Soc. 2009. PMID: 19591470 Free PMC article.
-
Unique biomedical application of fluorescence derivatization based on palladium-catalyzed coupling reactions for HPLC analysis of pharmaceuticals and biomolecules.Biomed Chromatogr. 2024 Jul;38(7):e5857. doi: 10.1002/bmc.5857. Epub 2024 Mar 20. Biomed Chromatogr. 2024. PMID: 38509750 Review.
-
Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction.Chemistry. 2021 Sep 24;27(54):13481-13493. doi: 10.1002/chem.202101880. Epub 2021 Aug 9. Chemistry. 2021. PMID: 34269488 Free PMC article. Review.